Synthesis of diospongin A

被引:49
作者
Bates, Roderick W. [1 ]
Song, Ping [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore
关键词
D O I
10.1016/j.tet.2007.03.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthesis of Diospongin A using a cross-metathesis-intramolecular Michael addition has been achieved. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4497 / 4499
页数:3
相关论文
共 19 条
[1]   Intramolecular Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double-bond geometry in controlling the diastereoselectivity of cyclizations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].
Banwell, MG ;
Bissett, BD ;
Bui, CT ;
Pham, HTT ;
Simpson, GW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (01) :9-18
[2]   Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].
Banwell, MG ;
Bui, CT ;
Pham, HTT ;
Simpson, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :967-969
[3]   CARBONATE EXTENSION - A VERSATILE PROCEDURE FOR FUNCTIONALIZATION OF ACYCLIC HOMOALLYLIC ALCOHOLS WITH MODERATE STEREOCONTROL [J].
BARTLETT, PA ;
MEADOWS, JD ;
BROWN, EG ;
MORIMOTO, A ;
JERNSTEDT, KK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4013-4018
[4]  
Bates R. W., manuscript in preparation
[5]   Total synthesis of polycavernoside A, a lethal toxin of the red alga Polycavernosa tsudai [J].
Blakemore, PR ;
Browder, CC ;
Hong, J ;
Lincoln, CM ;
Nagornyy, PA ;
Robarge, LA ;
Wardrop, DJ ;
White, JD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5449-5460
[7]   REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF EPOXY ALCOHOLS AND TRIOLS FROM ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA IODO CARBONATES [J].
BONGINI, A ;
CARDILLO, G ;
ORENA, M ;
PORZI, G ;
SANDRI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4626-4633
[8]   A general protocol for the regio high yielding opening of different glycidol derivatives [J].
Bonini, C ;
Chiummiento, L ;
Lopardo, MT ;
Pullez, M ;
Colobert, F ;
Solladié, G .
TETRAHEDRON LETTERS, 2003, 44 (13) :2695-2697
[9]   A short and efficient synthesis of (-)-diospongin A [J].
Bressy, Cyril ;
Allais, Florent ;
Cossy, Janine .
SYNLETT, 2006, (20) :3455-3456
[10]   Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: a new synthesis of substituted triazoles [J].
Chandrasekhar, S ;
Basu, D ;
Rambabu, C .
TETRAHEDRON LETTERS, 2006, 47 (18) :3059-3063