Formal total synthesis of (+)-didemniserinolipid B

被引：15

作者：

Prasad, Kavirayani R. ^{[1
]}

Gandi, Vasudeva Rao ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 23期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; ACID;

D O I：

10.1016/j.tetasy.2010.11.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2848 / 2852

页数：5

共 18 条

[1]

Kiyota H, 2006, V5

[2] Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp. [J].

Kiyota, H ;

Dixon, DJ ;

Luscombe, CK ;

Hettstedt, S ;

Ley, SV .

ORGANIC LETTERS, 2002, 4 (19) :3223-3226

[3] Synthesis of (+)-Didemniserinolipid B: Application of a 2-Allyl-4-fluorophenyl Auxiliary for Relay Ring-Closing Metathesis [J].

Marvin, Christopher C. ;

Voight, Eric A. ;

Suh, Judy M. ;

Paradise, Christopher L. ;

Burke, Steven D. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8452-8457

[4] Synthesis of (+)-didemniserinolipid B via ketalization/ring-closing metathesis [J].

Marvin, Christopher C. ;

Voight, Eric A. ;

Burke, Steven D. .

ORGANIC LETTERS, 2007, 9 (26) :5357-5359

[5] Cyclodidemniserinol trisulfate, a sulfated serinolipid from the Palauan ascidian Didemnum guttatum that inhibits HIV-1 integrase [J].

Mitchell, SS ;

Rhodes, D ;

Bushman, FD ;

Faulkner, DJ .

ORGANIC LETTERS, 2000, 2 (11) :1605-1607

[6] Stereoselective total synthesis of (+)-pinellic acid from L-(+)-tartaric acid [J].

Prasad, Kavirayani R. ;

Swain, Bandita .

TETRAHEDRON-ASYMMETRY, 2008, 19 (09) :1134-1138

[7] Stereoselective total synthesis of (+)-cardiobutanolide [J].

Prasad, Kavirayani R. ;

Gholap, Shivajirao L. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2916-2919

[8] Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)-etharvensin [J].

Prasad, Kavirayani R. ;

Gholap, Shivajirao L. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :2-11

[9] Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [Jaspine B] [J].

Prasad, Kavirayani R. ;

Chandrakumar, Appayee .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6312-6315

[10] Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol [J].

Prasad, Kavirayani R. ;

Chandrakumar, Appayee .

TETRAHEDRON, 2007, 63 (08) :1798-1805

← 1 2 →