Rhodium catalysed conjugate addition of a chiral alkenyltrifluoroborate salt: the enantioselective synthesis of hermitamides A and B

被引：17

作者：

Frost, Christopher G. ^{[1
]}

Penrose, Stephen D. ^{[1
]}

Gleave, Robert ^{[2
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] GlaxoSmithKline Inc, Gastrointestinal Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1039/b812897a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The concise enantioselective synthesis of hermitamides A and B is presented utilising a rhodium catalysed conjugate addition reaction to introduce the side chain and chiral information in a single step via an alkenyltrifluoroborate salt.

引用

页码：4340 / 4347

页数：8

共 55 条

[1] Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts [J].

Batey, RA ;

Quach, TD .

TETRAHEDRON LETTERS, 2001, 42 (52) :9099-9103

[2] STEREOSELECTIVE SYNTHESIS OF BETA-ALKOXY-ACRYLIC AND BETA-ALKYLTHIO-ACRYLIC ESTERS AND AMIDES FROM BETA-TOSYLACRYLIC DERIVATIVES [J].

BLAYA, S ;

CHINCHILLA, R ;

NAJERA, C .

TETRAHEDRON, 1995, 51 (12) :3617-3626

[3] A silicon-centred tetrafunctionalised reagent for the cyclopropylmethylsilane-terminated prins reaction and a concise synthesis of lyngbic acid [J].

Braddock, DC ;

Matsuno, A .

SYNLETT, 2004, (14) :2521-2524

[4] (-)-TRANS-7(S)-METHOXYTETRADEC-4-ENOIC ACID AND RELATED AMIDES FROM MARINE CYANOPHYTE LYNGBYA-MAJUSCULA [J].

CARDELLINA, JH ;

DALIETOS, D ;

MARNER, FJ ;

MYNDERSE, JS ;

MOORE, RE .

PHYTOCHEMISTRY, 1978, 17 (12) :2091-2095

[5] First stereoselective synthesis of serinol-derived malyngamides and their 1′-epi-isomers [J].

Chen, Jie ;

Li, Yang ;

Cao, Xiao-Ping .

TETRAHEDRON-ASYMMETRY, 2006, 17 (06) :933-941

[6] 2 EFFICIENT METHODS FOR THE CLEAVAGE OF PINANEDIOL BORONATE ESTERS YIELDING THE FREE BORONIC ACIDS [J].

COUTTS, SJ ;

ADAMS, J ;

KROLIKOWSKI, D ;

SNOW, RJ .

TETRAHEDRON LETTERS, 1994, 35 (29) :5109-5112

[7] Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].

Darses, S ;

Genet, JP .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327

[8] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[9] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

[10] Malyngamides O and P from the sea hare Stylocheilus longicauda [J].

Gallimore, WA ;

Scheuer, PJ .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (10) :1422-1424

← 1 2 3 4 5 6 →