Stereoselective total synthesis of Patulolide C

被引：5

作者：

Pratapareddy, Bommareddy ^{[1
]}

Sreenivasulu, Reddymasu ^{[2
]}

Rao, Mandava Venkata Basaveswara ^{[1
]}

Raju, Rudraraju Ramesh ^{[3
]}

机构：

[1] Krishna Univ, Dept Chem, Machilipatnam, Andhra Pradesh, India

[2] Jawaharlal Nehru Technol Univ, Dept Chem, Univ Coll Engn Autonomous, Kakinada, Andhra Pradesh, India

[3] Acharya Nagarjuna Univ, Dept Chem, Guntur, Andhra Pradesh, India

来源：

NATURAL PRODUCT RESEARCH | 2020年 / 34卷 / 19期

关键词：

(S)-chiral epoxide; ring opening of chiral epoxide; 1; 2-diol cleavage; stereoselective total synthesis; Patulolide C; (+)-PATULOLIDE C; CONVERSION; MACROLIDES;

D O I：

10.1080/14786419.2019.1586695

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Stereoselective total synthesis of Patulolide C has been accomplished from easily available and inexpensive (S)-chiral epoxide. The key steps involved in the concise synthesis of Patulolide C utilizes ring opening of chiral epoxide, cleavage of 1,2-diol, deprotection of benzyl ether of hydroxyl acid and Yamaguchi macrolactonisation dilution conditions as key steps. The advantage of this method include inexpensive starting material, mild reaction conditions and high purity of products.

引用

页码：2760 / 2764

页数：5

共 30 条

[1] A concise stereoselective total synthesis of (-)-cephalosporolide D [J].

Alluraiah, Gurrala ;

Sreenivasulu, Reddymasu ;

Sadanandam, Palle ;

Anitha, Kowthalam ;

Raju, Rudraraju Ramesh .

MONATSHEFTE FUR CHEMIE, 2016, 147 (02) :451-455

[2] Stereoselective total synthesis of verbalactone [J].

Alluraiah, Gurrala ;

Sreenivasulu, Reddymasu ;

Murthy, Indraganti Sreenivasa ;

Raju, Rudraraju Ramesh .

MONATSHEFTE FUR CHEMIE, 2014, 145 (12) :2019-2024

[3] Total synthesis of patulolide C and 11-epipatulolide C [J].

Babu, Kagita Veera ;

Sharma, Gangavaram. V. M. .

TETRAHEDRON-ASYMMETRY, 2008, 19 (05) :577-583

[4] Saturated and unsaturated lactones [J].

Collins, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11) :1377-1395

[5] Synthesis of (+)-Patulolide C Using R-(+)-γ-Valerolactone as a Chiral Synthon. [J].

Datrika, Rajender ;

Kallam, Srinivasa Reddy ;

Gajare, Vikas ;

Khobare, Sandip ;

Rama, Veera Swamy ;

Kommi, Muralikrishna ;

Hindupur, Rama Mohan ;

Vidavulur, Siddaiah ;

Tadikonda, Pratap V. .

CHEMISTRYSELECT, 2017, 2 (21) :5828-5831

[6] 1,8-stereocontrol by 1,5-induction using an allylstannane followed by Ireland-Claisen rearrangement:: Diastereoselective total synthesis of (±)-patulolide C [J].

Dorling, EK ;

Thomas, EJ .

TETRAHEDRON LETTERS, 1999, 40 (03) :471-474

[7] Stereoselective total synthesis of (-)-(5S,8R,13S,16R)-pyrenophorol [J].

Edukondalu, Perugu ;

Sreenivasulu, Reddymasu ;

Chiranjeevi, Barreddi ;

Kumar, Vuppula Naresh ;

Raju, Rudraraju Ramesh .

MONATSHEFTE FUR CHEMIE, 2015, 146 (08) :1309-1314

[8] The synthesis of (±)-patulolide C and its epimer via dodec-3-en-11-olide [J].

Kaisalo, L ;

Koskimies, J ;

Hase, T .

SYNTHETIC COMMUNICATIONS, 1999, 29 (03) :399-407

[9] Efficient conditions for conversion of 2-substituted furans into 4-oxygenated 2-enoic acids and its application to synthesis of (+)-aspicilin, (+)-patulolide A, and (-)-pyrenophorin [J].

Kobayashi, Y ;

Nakano, M ;

Kumar, GB ;

Kishihara, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7505-7515

[10] An alternative total synthesis of Patulolide A [J].

Konidena, Lakshmi Narayana Sharma ;

Chettu, Suresh Kumar ;

Mukkavilli, Praveena ;

Valluru, Krishna Reddy ;

Rao, Kameswara N. S. ;

Nowduri, Annapurna ;

Korupolu, Raghu Babu .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2019, 66 (02) :226-230

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