Work

11-Step Total Synthesis of Pallambins C and D

Year: 2016

Type: article

Abstract: The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6b04816

Authors: Luisruben P. Martinez, Shigenobu Umemiya, Sarah E. Wengryniuk, Phil S. Baran

Institution: Scripps Research Institute

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, National Institutes of Health, Japan Society for the Promotion of Science, National Institute of General Medical Sciences