Synthesis of the C1-C11 segment of tedanolide via vinylogous mukaiyama aldol reaction

被引:0
作者
Hassfeld, J [1 ]
Kalesse, M [1 ]
机构
[1] Free Univ Berlin, Fachbereich Organ Chem, Inst Chem, D-14195 Berlin, Germany
关键词
aldol reactions; Mukaiyama; natural products; dihydroxylations; stereoselective synthesis;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The successful construction of complex natural products depends to a large extent on how efficiently key intermediates can be generated. Here we report our efforts towards the first total synthesis of tedanolide (1), employing Evans' aldol methodology in combination with a vinylogous Mukaiyama aldol reaction (VMAR) and Sharpless' asymmetric dihydroxylation. This protocol allows for rapid access to its numerous chiral centers.
引用
收藏
页码:2007 / 2010
页数:4
相关论文
共 32 条
[1]   The first total synthesis of (+)-ratjadone [J].
Bhatt, U ;
Christmann, M ;
Quitschalle, M ;
Claus, E ;
Kalesse, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1885-1893
[2]  
Christmann M, 2000, ANGEW CHEM INT EDIT, V39, P4364, DOI 10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO
[3]  
2-G
[4]   Vinylogous Mukaiyama aldol reactions with triarylboranes [J].
Christmann, M ;
Kalesse, M .
TETRAHEDRON LETTERS, 2001, 42 (07) :1269-1271
[5]  
Christmann M., 2000, ANGEW CHEM, V112, P4535, DOI 10.1002/1521-3757(20001201)112:233.0.co
[6]  
2-k
[7]   BIOACTIVE MARINE METABOLITES .35. CYTOTOXIC METABOLITES OF THE MARINE SPONGE MYCALE-ADHAERENS LAMBE [J].
FUSETANI, N ;
SUGAWARA, T ;
MATSUNAGA, S ;
HIROTA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4971-4974
[8]   Advances in the vinylogous Mukaiyama aldol reaction and its application to the synthesis of the C1-C7 subunit of oleandolide [J].
Hassfeld, J ;
Kalesse, M .
TETRAHEDRON LETTERS, 2002, 43 (29) :5093-5095
[9]   Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions [J].
Hassfeld, J ;
Christmann, M ;
Kalesse, M .
ORGANIC LETTERS, 2001, 3 (22) :3561-3564
[10]   THREO ERYTHRO-ASSIGNMENT OF 1,3-DIOL DERIVATIVES BASED ON C-13 NMR-SPECTRA [J].
HOFFMANN, RW ;
WEIDMANN, U .
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (10) :3980-3992