Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions

被引：33

作者：

Singh, S ^{[1
]}

Han, H ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 33期

基金：

美国国家卫生研究院;

关键词：

polyhydroxylated pyrrolidines; regioselective asymmetric ammohydroxylation; allylic epoxidation; intramolecular cyclization;

D O I：

10.1016/j.tetlet.2004.06.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)(2)/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting 8-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6349 / 6352

页数：4

共 50 条

[31] First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization
Enders, D
del Signore, G
Berner, OM
CHIRALITY, 2003, 15 (06) : 510 - 513
[32] Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations
Natori, Yoshihiro
Kikuchi, Shunsuke
Kondo, Takahiro
Saito, Yukako
Yoshimura, Yuichi
Takahata, Hiroki
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (12) : 1983 - 1994
[33] Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling
Hornillos, Valentin
van Zijl, Anthoni W.
Feringa, Ben L.
CHEMICAL COMMUNICATIONS, 2012, 48 (31) : 3712 - 3714
[34] First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (-)-epocarbazolin A via Shi epoxidation
Knoell, Jan
Knoelker, Hans-Joachim
TETRAHEDRON LETTERS, 2006, 47 (34) : 6079 - 6082
[35] Simple Strategy for Benzo[de]chromene-7,8-dione Synthesis via Tandem Sonogashira Coupling and Intramolecular Cyclization Reactions
Yokoya, Masashi
Ishiguro, Takaaki
Sakairi, Yoshiaki
Kimura, Shinya
Morita, Yuji
Yamanaka, Masamichi
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (11)
[36] ASYMMETRIC TOTAL SYNTHESIS OF TACAMONINE (PSEUDOVINCAMONE-I) VIA RADICAL CYCLIZATION
IHARA, M
SETSU, F
SHOHDA, M
TANIGUCHI, N
TOKUNAGA, Y
FUKUMOTO, K
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18): : 5317 - 5323
[37] Concise asymmetric total synthesis of lycopodine and flabelliformine via cascade cyclization reaction
Wada, Kentaro
Kogure, Noriyuki
Kitajima, Mariko
Takayama, Hiromitsu
TETRAHEDRON LETTERS, 2019, 60 (02) : 187 - 190
[38] Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization.
Ohshima, T
Xu, YJ
Takita, R
Shibasaki, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U161 - U161
[39] RECENT ADVANCES IN THE TOTAL SYNTHESIS OF STEROIDS VIA INTRAMOLECULAR CYCLOADDITION REACTIONS
KAMETANI, T
NEMOTO, H
TETRAHEDRON, 1981, 37 (01) : 3 - 16
[40] PALLADIUM-CATALYZED INTRAMOLECULAR ASYMMETRIC ENE REACTIONS OF CHIRAL ALLYLIC SULFONES VIA CHIRAL ALLYLIC SULFINATE-SULFONE REARRANGEMENTS
HIROI, K
KURIHARA, Y
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) : 1778 - 1780

← 1 2 3 4 5 →