Construction of the [6-7-5-5] tetracyclic core of all the carbocyclic frameworks of yuzurimine-type alkaloids

Ichiro Hayakawa; Keisuke Niida; Hideo Kigoshi

doi:10.1039/c5cc03479e

Construction of the [6-7-5-5] tetracyclic core of all the carbocyclic frameworks of yuzurimine-type alkaloids

Chem Commun (Camb). 2015 Jul 25;51(58):11568-71. doi: 10.1039/c5cc03479e. Epub 2015 Jun 22.

Authors

Ichiro Hayakawa¹, Keisuke Niida, Hideo Kigoshi

Affiliation

¹ Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan. ichiro.hayakawa@okayama-u.ac.jp.

PMID: 26097917
DOI: 10.1039/c5cc03479e

Abstract

Yuzurimine-type alkaloids make up a sub-family of Daphniphyllum alkaloids structurally featuring a [6-7-5-5] tetracarbocyclic core framework. In this manuscript, we describe our construction of the [6-7-5-5] tetracarbocyclic core of yuzurimine-type alkaloids by using a unique in situ intramolecular Wittig reaction and Sm-mediated cyclization as key steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Cyclization
Magnoliopsida

Substances

Alkaloids