Total Synthesis of Cochlearol B via Intramolecular [2+2] Photocycloaddition

被引：19

作者：

Mashiko, Tomoya ^{[1
]}

Shingai, Yuta ^{[1
]}

Sakai, Jun ^{[1
]}

Kamo, Shogo ^{[1
]}

Adachi, Shinya ^{[1
]}

Matsuzawa, Akinobu ^{[1
]}

Sugita, Kazuyuki ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Dept Synthet Med Chem, Shinagawa Ku, 2-4-41 Ebara, Tokyo 1428501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 46期

关键词：

cochlearol B; intramolecular [2+2] photocycloaddition; natural product; oxidative cyclization; total synthesis; CONSTRUCTION; EFFICIENT; GANODERMA; BONDS;

D O I：

10.1002/anie.202110556

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we describe the first total synthesis of cochlearol B, a meroterpenoid natural product featuring a 4/5/6/6/6-fused pentacyclic structure. Key steps, oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition, which constructed the pentacyclic structure in highly stereoselective manner, allowed efficient access to cochlearol B with the longest linear sequence of 16 steps, and in 9 % overall yield. Single-crystal X-ray crystallographic analysis clearly confirmed the stereochemistry of cochlearol B.

引用

页码：24484 / 24487

页数：4

共 50 条

[1] Total Synthesis of (+)-Lactiflorin by an Intramolecular [2+2] Photocycloaddition
Lu, Ping
Bach, Thorsten
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (05) : 1261 - 1264
[2] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-STOECHOSPERMOL VIA STEREOSELECTIVE INTRAMOLECULAR (2+2)-PHOTOCYCLOADDITION OF THE CHIRAL BUTENOLIDE
TANAKA, M
TOMIOKA, K
KOGA, K
[J]. TETRAHEDRON, 1994, 50 (45) : 12829 - 12842
[3] Synthesis of cyclobutanetricarboxylic acid derivatives via intramolecular [2+2] photocycloaddition
Braussaud, N
Hoffmann, N
Scharf, HD
[J]. TETRAHEDRON, 1997, 53 (43) : 14701 - 14712
[4] Synthesis of cyclobutanetricarboxylic acid derivatives via intramolecular [2+2] photocycloaddition
[J]. Tetrahedron, 43 (14701):
[5] ASYMMETRIC TOTAL SYNTHESIS OF STOECHOSPERMOL USING INTRAMOLECULAR (2+2) PHOTOCYCLOADDITION REACTION
TANAKA, M
TOMIOKA, K
KOGA, K
[J]. TETRAHEDRON LETTERS, 1985, 26 (25) : 3035 - 3038
[6] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF VINYLARENES - SYNTHESIS OF CYCLOPHANES
NISHIMURA, J
OKADA, Y
INOKUMA, S
NAKAMURA, Y
GAO, SR
[J]. SYNLETT, 1994, (11) : 884 - 894
[7] An intramolecular [2+2] photocycloaddition-fragmentation approach towards the total synthesis of asteriscanolide
BookerMilburn, KI
Cowell, JK
[J]. TETRAHEDRON LETTERS, 1996, 37 (13) : 2177 - 2180
[8] Synthesis of [2.n]thiophenophanes by intramolecular [2+2] photocycloaddition
Nakamura, Y
Kaneko, M
Shinmyozu, T
Nishimura, J
[J]. HETEROCYCLES, 1999, 51 (05) : 1059 - 1065
[9] SYNTHETIC STUDIES ON CAROTANE AND DOLASTANE TYPE TERPENES - A NEW ENTRY TO THE TOTAL SYNTHESIS OF (+/-)-DAUCENE VIA INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION
SETO, H
FUJIMOTO, Y
TATSUNO, T
YOSHIOKA, H
[J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (14) : 1217 - 1224
[10] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF OXOESTERS AND OXOAMIDES
LEBLANC, S
PETE, JP
PIVA, O
[J]. TETRAHEDRON LETTERS, 1993, 34 (04) : 635 - 638

← 1 2 3 4 5 →