Catalytic, asymmetric synthesis of siphonarienal

被引:43
作者
Calter, MA [1 ]
Liao, WS [1 ]
Struss, JA [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
关键词
D O I
10.1021/jo0160367
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.
引用
收藏
页码:7500 / 7504
页数:5
相关论文
共 31 条
[1]   Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary [J].
Abiko, A ;
Masamune, S .
TETRAHEDRON LETTERS, 1996, 37 (07) :1081-1084
[2]   TRIS(TRIMETHYLSILYL)SILANE AND DIPHENYLSILANE IN THE RADICAL CHAIN DIDEOXYGENATION OF 1,6-ANHYDRO-D-GLUCOSE - A COMPARATIVE-STUDY [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1992, 33 (44) :6629-6632
[3]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[4]  
BASHA A, 1977, TETRAHEDRON LETT, P4171
[5]   Novel polypropionates from the South African marine mollusc Siphonaria capensis [J].
Beukes, DR ;
Davies-Coleman, MT .
TETRAHEDRON, 1999, 55 (13) :4051-4056
[6]   The total synthesis of (+)-pectinatone: An iterative alkylation approach based on the SAMP-hydrazone method [J].
Birkbeck, AA ;
Enders, D .
TETRAHEDRON LETTERS, 1998, 39 (43) :7823-7826
[7]   STEREOSELECTIVE SYNTHESES OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES [J].
BOYD, SA ;
MANTEI, RA ;
HSIAO, CN ;
BAKER, WR .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :438-442
[8]   One-pot, catalytic, asymmetric synthesis of polypropionates [J].
Calter, MA ;
Guo, X ;
Liao, WS .
ORGANIC LETTERS, 2001, 3 (10) :1499-1501
[9]   One-pot, catalytic, asymmetric syntheses of all four stereoisomers of a dipropionate synthon [J].
Calter, MA ;
Guo, X .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5308-5309
[10]   NARGENICIN BIOSYNTHESIS - INCORPORATION OF POLYKETIDE CHAIN ELONGATION INTERMEDIATES AND SUPPORT FOR A PROPOSED INTRAMOLECULAR DIELS-ALDER CYCLIZATION [J].
CANE, DE ;
TAN, WT ;
OTT, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :527-535