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

[41] Control of the Intramolecular [2+2] Photocycloaddition in a Bis-Stilbene Macrocycle
Xu, Yuewen
Smith, Mark D.
Krause, Jeanette A.
Shimizu, Linda S.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (13): : 4874 - 4877
[42] REGIO AND STEREOCHEMISTRY IN 2+2 INTRAMOLECULAR PHOTOCYCLOADDITION OF SUBSTITUTED OLEFINS TO CYCLOPENTENONES
BECKER, D
KLIMOVICH, N
[J]. TETRAHEDRON LETTERS, 1994, 35 (02) : 261 - 264
[43] A Chiral Thiourea as a Template for Enantioselective Intramolecular [2+2] Photocycloaddition Reactions
Mayr, Florian
Brimioulle, Richard
Bach, Thorsten
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 6965 - 6971
[44] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF N-ALKENOYL BETA - ENAMINONES
AMOUGAY, A
PETE, JP
PIVA, O
[J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7347 - 7350
[45] STUDIES ON THE INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF DIHYDRO-4-PYRONES
HADDAD, N
KUSMENKOV, I
[J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 6127 - 6130
[46] Intramolecular [2+2] photocycloaddition of N-alkenoyl-beta-enaminones
Amougay, A
Pete, JP
Piva, O
[J]. BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1996, 133 (06): : 625 - 635
[47] THE PREPARATION OF PHOTORESPONSIVE CYCLOBUTANOCROWN ETHERS BY MEANS OF INTRAMOLECULAR [2+2]PHOTOCYCLOADDITION
AKABORI, S
KUMAGAI, T
HABATA, Y
SATO, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (07) : 2459 - 2466
[48] Construction of gel networks via [2+2] photocycloaddition
Zhao, Lei-Min
[J]. JOURNAL OF MATERIALS CHEMISTRY C, 2023, 11 (08) : 2826 - 2830
[49] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION .4. SYNTHESIS OF [4.N]CYCLOPHANES BY [2+2] PHOTOCYCLOADDITION AND BIRCH REDUCTION - A RARE FRAGMENTATION OF TETRAMETHYLENE RADICAL-ANION
NISHIMURA, J
OHBAYASHI, A
UEDA, E
OKU, A
[J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (11): : 2025 - 2028
[50] INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION OF 2-(ALKENYLOXY)CYCLOHEX-2-ENONES
IKEDA, M
TAKAHASHI, M
UCHINO, T
OHNO, K
TAMURA, Y
KIDO, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23): : 4241 - 4247

← 1 2 3 4 5 →