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- Title
Total Synthesis of Cochlearol B via Intramolecular [2+2] Photocycloaddition.
- Authors
Mashiko, Tomoya; Shingai, Yuta; Sakai, Jun; Kamo, Shogo; Adachi, Shinya; Matsuzawa, Akinobu; Sugita, Kazuyuki
- Abstract
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.
- Subjects
PHOTOCYCLOADDITION; MARINE natural products; NATURAL products; STEREOCHEMISTRY; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2021, Vol 133, Issue 46, p24689
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202110556