Synthetic Study of (-)-Norzoanthamine: Construction of the ABC Ring Moiety

被引：42

作者：

Murata, Yoshihisa ^{[1
]}

Yamashita, Daisuke ^{[1
]}

Kitahara, Katsushi ^{[1
]}

Minasako, Yohei ^{[1
]}

Nakazaki, Atsuo ^{[1
]}

Kobayashi, Susumu ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 08期

关键词：

diastereoselectivity; Diels-Alder reaction; Michael addition; natural products; total synthesis; ORGANIC-SYNTHESIS; ZOANTHAMINE/NORZOANTHAMINE ALKALOIDS; PHENYLDIMETHYLSILYL GROUP; CONVERSION; DIELS; NORZOANTHAMINE;

D O I：

10.1002/anie.200804544

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Throw your hat in the ring: A highly diastereoselective synthesis of the ABC rings of (-)-norzoanthamine has been achieved starting from the (-)-Hajos-Parrish ketone (see scheme). Three asymmetric quaternary carbon centers on the C ring were constructed by a 1,4-addition, and an intramolecular Diels-Alder reaction provided a trans-decalin scaffold on the AB rings. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1400 / 1403

页数：4

共 50 条

[1] Stereoselective synthesis of the ABC ring system of norzoanthamine
Ghosh, S
Rivas, F
Fischer, D
González, MA
Theodorakis, EA
ORGANIC LETTERS, 2004, 6 (06) : 941 - 944
[2] Synthetic study of fomitellic acids: construction of the AB ring moiety
Yamaoka, Makoto
Fukatsu, Yuichi
Nakazaki, Atsuo
Kobayashi, Susumu
TETRAHEDRON LETTERS, 2009, 50 (27) : 3849 - 3852
[3] Synthetic studies of zoanthamine/norzoanthamine alkaloids: Construction of the heterocyclic aminal core (CDEFG ring)
Hikage, N
Furukawa, H
Takao, K
Kobayashi, S
TETRAHEDRON LETTERS, 1998, 39 (34) : 6241 - 6244
[4] Synthetic studies of norzoanthamine. Preparation of the diene-yne-diene precursor of an ABC-ring fragment
Irifune, T
Ohashi, T
Ichino, T
Sakai, E
Suenaga, K
Uemura, D
CHEMISTRY LETTERS, 2005, 34 (07) : 1058 - 1059
[5] Synthetic studies of zoanthamine alkaloids. Stereoselective synthesis of the ABC ring system of norzoanthamine by an intramolecular Diels-Alder reaction
Sakai, M
Sasaki, M
Tanino, K
Miyashita, M
TETRAHEDRON LETTERS, 2002, 43 (09) : 1705 - 1708
[6] Synthetic studies on manzamine A: Construction of the tricyclic ABC ring subunit I
Li, SM
Ohba, S
Kosemura, S
Yamamura, S
TETRAHEDRON LETTERS, 1996, 37 (41) : 7365 - 7368
[7] SYNTHETIC STUDY OF AFRITOXINONE A: STEREOSELECTIVE CONSTRUCTION OF FUROPYRANONE MOIETY
Abe, Hideki
Yoshie, Toshihiro
Wagatsuma, Takumi
Kobayashi, Toyoharu
Ito, Hisanaka
HETEROCYCLES, 2015, 90 (01) : 706 - 714
[8] Synthetic Study on Azadirachtin (Part 2). Construction of the Decalin Moiety with Full Functionality on B-ring
Watanabe, H.
Watanabe, T.
Mori, K.
Kitahara, T.
Tetrahedron Letters, 38 (25):
[9] Synthetic study on azadirachtin .2. Construction of the decalin moiety with full functionality on B-ring.
Watanabe, H
Watanabe, T
Mori, K
Kitahara, T
TETRAHEDRON LETTERS, 1997, 38 (25) : 4429 - 4432
[10] Enantioselective Synthesis of the ABC Ring Motif of Norzoanthamine Based on Asymmetric Robinson Annulation Reactions
Nguyen, Thong X.
Dakanali, Marianna
Trzoss, Lynnie
Theodorakis, Emmanuel A.
ORGANIC LETTERS, 2011, 13 (13) : 3308 - 3311

← 1 2 3 4 5 →