Structures and Synthesis of Hitoyopodins: Bioactive Aromatic Sesquiterpenoids Produced by the Mushroom Coprinopsis cinerea.

Abstract

The structures of sesquiterpenoids hitoyopodin A (1) and its hydroxy derivatives 2 and 3 from the mushroom Coprinopsis cinerea are reported. Their absolute structures (1-3) with a benzoxabicyclo[3.2.1]octane core were determined by spectroscopy, X-ray crystallography, and total synthesis of 1. Compound 1 displays antiproliferative activity against HL-60 cancer cells and the malarial parasite Plasmodium falciparum. It is proposed that 1 acts as a crucial precursor in the biosynthesis of 2, 3, and lagopodins.

• Authors: Junnosuke Otaka, Takeshi Shimizu, Yushi Futamura, Daisuke Hashizume, Hiroyuki Osada
• Journal: Organic letters (Org Lett) Vol. 20 Issue 19 Pg. 6294-6297 (10 05 2018) ISSN: 1523-7052 [Electronic] United States
• PMID: 30234313 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)