Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-cope prins cascade

被引：44

作者：

Dalgard, JE ^{[1
]}

Rychnovsky, SD ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 08期

关键词：

D O I：

10.1021/ol050270s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 2-oxonia-Cope Prins cascade was developed that led to a facile and stereoselective synthesis of the C18-C25 segment of lasonolide A. The strategy nicely handles the introduction of the quaternary center in the tetrahydropyran ring, and all of the stereogenic centers in the product arise from a single stereocenter introduced in a catalytic enantioselective reaction.

引用

页码：1589 / 1591

页数：3

共 50 条

[31] Synthetic studies on amphidinolides C and F: synthesis of the C18-C29 segment of amphidinolide F
Armstrong, Alan
Pyrkotis, Constantina
TETRAHEDRON LETTERS, 2009, 50 (26) : 3325 - 3328
[32] STUDIES DIRECTED TOWARD THE SYNTHESIS OF PHOMENOIC ACID .1. ENANTIOSELECTIVE SYNTHESIS OF THE C(1)-TO-C(6) SEGMENT
HASSAN, HHAM
TAMM, C
HELVETICA CHIMICA ACTA, 1994, 77 (03) : 838 - 849
[33] Progress directed toward the total synthesis of rhizoxin: Enantioselective synthesis of C12 to C26 segment.
Hong, J
Burke, SD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 560 - ORGN
[34] Synthetic studies directed towards epothilone A:: Enantioselective synthesis of a C7-C15 carboxaldehyde segment
Bijoy, P
Avery, MA
TETRAHEDRON LETTERS, 1998, 39 (3-4) : 209 - 212
[35] Enantioselective synthesis of the C11-C17 segment of soraphen A1α via organoiron methodology
Cao, YY
Eweas, AF
Donaldson, WA
TETRAHEDRON LETTERS, 2002, 43 (43) : 7831 - 7834
[36] An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921
Ghosh, Arun K.
Rodriguez, Samuel
TETRAHEDRON LETTERS, 2016, 57 (26) : 2884 - 2887
[37] STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF RHIZOXIN - STEREOSELECTIVE SYNTHESIS OF C-12 TO C-18 SEGMENT
RAO, AVR
BHANU, MN
SHARMA, GVM
TETRAHEDRON LETTERS, 1993, 34 (04) : 707 - 710
[38] Synthetic Studies Directed Towards Epothilone A: Enantioselective Synthesis of a C7-C15 Carbpxa;dejude Segment
Tetrahedron Lett, 3-4 (209):
[39] Stereoselective Synthesis of the C25-C36 Segment of Arenicolides A and B: Determination of the Configuration of the Trisubstituted Epoxide
Nagumo, Shinji
Nakano, Taeko
Hata, Kyomi
Mizukami, Megumi
Miyashita, Masaaki
ORGANIC LETTERS, 2010, 12 (05) : 908 - 911
[40] Enantioselective Polyol Synthesis via the Cope Rearrangement of Chiral Aldol Products. A Synthesis of the C1-C10-Fragment of Nystatin A1
Tetrahedron Lett, 1-2 (09):

← 1 2 3 4 5 →