Published February 2018 | Version Supplemental Material
Journal Article Open

Progress towards the total synthesis of hamigerans C and D: a direct approach to an elaborated 6-7-5 carbocyclic core

  • 1. ROR icon California Institute of Technology
  • 2. ROR icon Lundbeck (Denmark)

Abstract

The hamigeran family of natural products has been the target of numerous synthetic efforts because of its biological activity and interesting structural properties. Herein, we disclose our efforts toward the synthesis of hamigerans C and D, unique among the initially isolated members because of their 6-7-5 carbocyclic core. Our approach directly targets this tricyclic motif by sequential Negishi and Heck coupling reactions, yielding an advanced intermediate with all necessary carbons and sufficient functionality poised for completion of the synthesis of these two natural products.

Additional Information

© 2017 Japan Antibiotics Research Association. Received 8 June 2017; revised 3 July 2017; accepted 6 July 2017. Online publication, 6 September 2017. Dedicated to Prof K. C. Nicolaou for his tremendous scientific contributions to the total synthesis of highly complex and biologically important natural products. We thank NIH-NIGMS (R01GM080269) for supporting this research. DCD would like to thank the NSF (predoctoral research fellowship, No. DGE-1144469) and Caltech for financial support. Dr David VanderVelde (Caltech) is thanked for aid in NMR structural determination. Dr Allen Hong and Dr Scott Virgil are thanked for helpful discussions. The authors declare no conflict of interest.

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Additional details

Additional titles

Alternative title
Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core

Identifiers

PMCID
PMC5788718
Eprint ID
81215
DOI
10.1038/ja.2017.96
Resolver ID
CaltechAUTHORS:20170906-153516673

Related works

Describes
10.1038/ja.2017.96 (DOI)

Funding

NIH
R01GM080269
NSF Graduate Research Fellowship
DGE-1144469
Caltech

Dates

Created
2017-09-07
Created from EPrint's datestamp field
Updated
2022-03-22
Created from EPrint's last_modified field