Concise Diverted Total Synthesis of Amphidinolide T1 and T4 from a (12E)-Cycloalkene by Selective Functionalization of the C12-C13 Double Bond

被引：11

作者：

Sun, Lijie ^{[1
,2
]}

Wu, Dongdong ^{[3
]}

Wu, Jinlong ^{[3
]}

Dai, Wei-Min ^{[1
,2
,3
]}

机构：

[1] Hong Kong Univ Sci & Technol, Ctr Canc Res, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

[3] Zhejiang Univ, Dept Chem, Lab Asymmetr Catalysis & Synth, Hangzhou 310027, Peoples R China

来源：

SYNLETT | 2011年 / 20期

基金：

中国国家自然科学基金;

关键词：

alkenes; dihydroxylation; macrocycles; osmium; total synthesis; RING-CLOSING METATHESIS; OLEFIN-METATHESIS; NATURAL-PRODUCTS; SILYL MIGRATION; STEREOSELECTIVE-SYNTHESIS; 19-MEMBERED MACROLIDE; BIOACTIVE MACROLIDES; CONVENIENT SYNTHESIS; PROTECTING GROUPS; ORGANIC-SYNTHESIS;

D O I：

10.1055/s-0031-1289903

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from a 19-membered (12E)-cycloalkene prepared by ring-closing metathesis, amphidinolide T1 and T4 were efficiently synthesized via a short sequence of selective functionalization. The key steps highlighted stereoselective dihydroxylation of the (E)-C12-C13 double bond and highly regioselective silylation/desilylation of the (12S, 13S)-diol. In particular, a significant solvent effect was discovered for suppressing 1,4 O -> O silyl migration or disilylation during selective mono-silylation of the (12R, 13R)- and (12S, 13S)-diols in toluene. In combination with our previous synthesis of amphidinolide T3, the same (12E)-cycloalkene serves as an advanced common intermediate for concise diverted total synthesis of amphidinolide T family of marine macrolides.

引用

页码：3036 / 3040

页数：5

共 62 条

[1] Synthesis of the C1-C12 fragment of amphidinolide T1 [J].

Abbineni, Chandrasekhar ;

Sasmal, Pradip K. ;

Mukkanti, K. ;

Iqbal, Javed .

TETRAHEDRON LETTERS, 2007, 48 (24) :4259-4262

[2] Total syntheses of amphidinolide T1, T3, T4, and T5 [J].

Aïssa, C ;

Riveiros, R ;

Ragot, J ;

Fürstner, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15512-15520

[3] Total synthesis of fostriecin (CI-920) [J].

Boger, DL ;

Ichikawa, S ;

Zhong, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4161-4167

[4] A new synthesis of tetrahydrofuran fragment of amphidinolides X and Y [J].

Chen, Yile ;

Jin, Jian ;

Wu, Jinlong ;

Dai, Wei-Min .

SYNLETT, 2006, (08) :1177-1180

[5] Concise synthesis of the C-1-C-12 fragment of amphidinolides T1-T5 [J].

Clark, J. Stephen ;

Labre, Flavien ;

Thomas, Lynne H. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (13) :4823-4830

[6] Synthesis of amphidinolide T1 via catalytic, stereoselective macrocyclization [J].

Colby, EA ;

O'Brien, KC ;

Jamison, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :998-999

[7] Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations [J].

Colby, EA ;

O'Brien, KC ;

Jamison, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4297-4307

[8] Impact of Natural Products on Developing New Anti-Cancer Agents [J].

Cragg, Gordon M. ;

Grothaus, Paul G. ;

Newman, David J. .

CHEMICAL REVIEWS, 2009, 109 (07) :3012-3043

[9] Total synthesis of amphidinolide X and its 12Z-isomer by formation of the C12-C13 trisubstituted double bond via ring-closing metathesis [J].

Dai, Wei-Min ;

Chen, Yile ;

Jin, Jian ;

Wu, Jinlong ;

Lou, Jianshu ;

He, Qiaojun .

SYNLETT, 2008, (11) :1737-1741

[10] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

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