The first stereoselective synthesis of polyketide natural product (3R,6S)-6-hydroxylasiodiplodin (1) has been described starting from commonly available starting materials D-mannitol and 2,4,6-trihydroxybenzoic acid. The key reactions involved are Keck asymmetric allylation, Stille coupling, De Brabander's esterification, and ring-closing metathesis (RCM) reaction. The total synthesis was achieved in 19.3% overall yield making the route significant. (C) 2016 Elsevier Ltd. All rights reserved.
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Feng Yong-Kui
Su Hua-Lan
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Su Hua-Lan
Mukula Otukol, Billy Joel
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Mukula Otukol, Billy Joel
Zhang Xue-Qing
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Zhang Xue-Qing
Yao Hui
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Yao Hui
Huang Nian-Yu
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
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Univ Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, Italy
Zullo, Valerio
Petri, Antonella
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Univ Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, Italy
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Indian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, India
Madhan, A
Rao, BV
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Indian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, India
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Feng Yong-Kui
Su Hua-Lan
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Su Hua-Lan
Mukula Otukol, Billy Joel
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Mukula Otukol, Billy Joel
Zhang Xue-Qing
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Zhang Xue-Qing
Yao Hui
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
Yao Hui
Huang Nian-Yu
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China Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R ChinaChina Three Gorges Univ, Coll Biol & Pharmaceut Sci, China Natl Light Ind, Hubei Key Lab Nat Prod Res & Dev,Key Lab Funct Ye, Yichang 443002, Hubei, Peoples R China
机构:
Univ Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, Italy
Zullo, Valerio
Petri, Antonella
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Univ Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via Giuseppe Moruzzi 13, I-56124 Pisa, Italy
机构:
Indian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, India
Madhan, A
Rao, BV
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Indian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, IndiaIndian Inst Chem Technol, Organ div 3, Hyderabad 500007, Andhra Pradesh, India