Stereoselective synthesis of the dolastatin units by organotrifluoroborates additions to α-amino aldehydes

被引：23

作者：

Cella, Rodrigo ^{[1
]}

Venturoso, Raphael C. ^{[2
]}

Stefani, Helio A. ^{[1
,2
]}

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05508 Sao Paulo, Brazil

[2] Univ Sao Paulo, Fac Ciencias Farmaceut, BR-05508 Sao Paulo, Brazil

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 01期

关键词：

D O I：

10.1016/j.tetlet.2007.11.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dolastatin units were synthesized from the 1,2-addition reactions of potassium allyl or crotyltrifluoroborate salts to aldehyde derivatives from natural amino acids. The reactions were carried out in presence of a phase-transfer catalyst in a biphasic medium at room temperature and excellent yields (>89-93%) and stereoselective (>90:10 to 98:2) were obtained. The dolastatin units 8 and 14a-b were obtained after three steps in good overall yields (50-62%). (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：16 / 19

页数：4

共 34 条

[1] An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction [J].

Almeida, WP ;

Coelho, F .

TETRAHEDRON LETTERS, 2003, 44 (05) :937-940

[2]

BAGNIEWSKI PG, 1997, P AM ASSOC CANC RES, V38, P2221

[3] Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation [J].

Batey, RA ;

Thadani, AN ;

Smil, DV .

TETRAHEDRON LETTERS, 1999, 40 (23) :4289-4292

[4]

Batey RA, 2000, SYNTHESIS-STUTTGART, P990

[5] Synthesis of permethylated α-D-mannosylacetic acid, a new type of bioconjugate [J].

Brunel, FM ;

Taylor, KG ;

Spatola, AF .

TETRAHEDRON LETTERS, 2003, 44 (06) :1287-1289

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

Darses, S ;

Genet, JP .

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

[7]

Dias LC, 2003, SYNTHESIS-STUTTGART, P603

[8]

Gerwick WH, 2001, ALKALOIDS, V57, P75, DOI 10.1016/S0099-9598(01)57003-0

[9]

HAMADA Y, 1982, CHEM PHARM BULL, V30, P1921

[10] STEREOSELECTIVE ADDITION OF LITHIOETHYL ACETATE TO BOC-L-PROLINAL - A CONVENIENT CHIRAL SYNTHETIC BUILDING BLOCK FOR THE PYRROLIZIDINE ALKALOID RING-SYSTEM [J].

HANSON, GJ ;

BARAN, JS ;

LINDBERG, T .

TETRAHEDRON LETTERS, 1986, 27 (31) :3577-3580

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