Synthetic study of fomitellic acids: construction of the AB ring moiety

被引：26

作者：

Yamaoka, Makoto ^{[1
]}

Fukatsu, Yuichi ^{[1
]}

Nakazaki, Atsuo ^{[1
]}

Kobayashi, Susumu ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Pharmaceut Sci, RIKADAI, Noda, Chiba 2788510, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 27期

基金：

日本学术振兴会;

关键词：

Titanium(III)-mediated radical cascade cyclization; Epoxypolyene; Vinylogous Mukaiyama aldol reaction; Triterpenoid; 1ST TOTAL-SYNTHESIS; CATALYTIC EPOXYPOLYENE CYCLIZATION; DNA-POLYMERASE; STRAIGHTFORWARD SYNTHESIS; STRUCTURAL DETERMINATION; RADICAL CYCLIZATIONS; REVISED STRUCTURES; TERPENOIDS; PALMEROLIDE; TITANOCENE(III);

D O I：

10.1016/j.tetlet.2009.04.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereocontrolled synthesis of a fully functionalized AB ring moiety of fomitellic acids was accomplished. The tricyclic skeleton was stereoselectively constructed by means of titanium(III)-mediated radical cascade cyclization of epoxypolyene. The stereochemistry at C1 and C3 was controlled by a vinylogous Mukaiyama aldol reaction and a Sharpless asymmetric epoxidation, respectively. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3849 / 3852

页数：4

共 50 条

[21] SYNTHESIS OF THE BICYCLO[5.3.1]UNDECANE MOIETY (AB RING-SYSTEM) OF TAXANES
SNIDER, BB
ALLENTOFF, AJ
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01): : 321 - 328
[22] Synthetic Strategies for Peroxide Ring Construction in Artemisinin
Vil', Vera A.
Yaremenko, Ivan A.
Ilovaisky, Alexey I.
Terent'ev, Alexander O.
MOLECULES, 2017, 22 (01):
[23] Synthetic study towards azadirachtin: An efficient and stereoselective construction of the AB rings with full functionality
Watanabe, Hidenori
Mori, Naoki
Itoh, Daisuke
Kitahara, Takeshi
Mori, Kenji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) : 1512 - 1516
[24] Synthetic studies on azadirachtin: Construction of the highly functionalized decalin moiety of azadirachtin
Ishihara, J
Yamamoto, Y
Kanoh, N
Murai, A
TETRAHEDRON LETTERS, 1999, 40 (23) : 4387 - 4390
[25] Stereoselective synthesis of the optically pure AB-ring moiety of trichothecene sesquiterpene (+)-calonectrin
Iida, A
Konishi, K
Matsumoto, H
Kaneko, M
Tomioka, K
HETEROCYCLES, 2003, 59 (02) : 595 - 604
[26] Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety
Noguchi, N
Nakada, M
ORGANIC LETTERS, 2006, 8 (10) : 2039 - 2042
[27] Synthetic Study on Acremoxanthone A: Construction of Bicyclo [3.2.2]nonane CD Skeleton and Fusion of AB Rings
Hirano, Yoichi
Tokudome, Kensei
Takikawa, Hiroshi
Suzuki, Keisuke
SYNLETT, 2017, 28 (02) : 214 - 220
[28] A new route for the construction of the AB-ring core of Taxol
Shimada, Y
Nakamura, M
Suzuka, T
Matsui, J
Tatsumi, R
Tsutsumi, K
Morimoto, T
Kurosawa, H
Kakiuchi, K
TETRAHEDRON LETTERS, 2003, 44 (07) : 1401 - 1403
[29] ALTERNATE METHOD FOR CONSTRUCTION OF VERNOLEPIN AB-RING SYSTEM
GRIECO, PA
REAP, JJ
NOGUEZ, JA
SYNTHETIC COMMUNICATIONS, 1975, 5 (02) : 155 - 159
[30] SYNTHETIC STRATEGY FOR CONSTRUCTION OF THE FURANOHYDROPHENANTHRENE RING-SYSTEM
BABA, Y
SAKAMOTO, T
KANEMATSU, K
TETRAHEDRON LETTERS, 1994, 35 (31) : 5677 - 5680

← 1 2 3 4 5 →