A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599-Reference-Cited by-同舟云学术

A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599

Published:2020 Issue:23 Volume:11 Page:5929-5934
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Roque Jose B.¹²³⁴^ORCID,Mercado-Marin Eduardo V.¹²³⁴,Richter Sven C.¹²³⁴,Pereira de Sant'Ana Danilo¹²³⁴,Mukai Ken¹²³⁴,Ye Yingda¹²³⁴,Sarpong Richmond¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry

2. University of California

3. Berkeley

4. USA

Abstract

A route that has resulted in the synthesis of preparaherquamide, (+)-VM-55599, and premalbrancheamide using a common intermediate is reported.

Funder

National Institute of General Medical Sciences

Bristol-Myers Squibb

Japan Society for the Promotion of Science

Conselho Nacional de Desenvolvimento Científico e Tecnológico

National Science Foundation

American Chemical Society

Hellman Foundation

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/SC/D0SC02296A

Reference38 articles.

1. Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

2. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids

3. Asymmetric Total Synthesis of (−)-VM55599: Establishment of the Absolute Stereochemistry and Biogenetic Implications

4. Total Synthesis of VM55599. Utilization of an Intramolecular Diels−Alder Cycloaddition of Potential Biogenetic Relevance

5. Concise, biomimetic total synthesis of d,l-marcfortine C

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