Intramolecular allenolate acylations in studies toward a synthesis of FR182877

C D Vanderwal; D A Vosburg; E J Sorensen

doi:10.1021/ol016994v

Intramolecular allenolate acylations in studies toward a synthesis of FR182877

Org Lett. 2001 Dec 27;3(26):4307-10. doi: 10.1021/ol016994v.

Authors

C D Vanderwal¹, D A Vosburg, E J Sorensen

Affiliation

¹ The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

PMID: 11784204
DOI: 10.1021/ol016994v

Abstract

During our efforts to synthesize the cytotoxic natural product FR182877, we discovered intramolecular reductive acylations that offer a stereocontrolled alternative to the classical Knoevenagel condensation for the formation of alpha-alkylidene beta-keto-delta-lactones. Other progress toward a synthesis of FR182877 includes a pi-allyl Stille coupling and a bromo Horner-Wadsworth-Emmons reaction that forms a 12-membered ring. Structural relationships among FR182877, hexacyclinic acid, macquarimicin A, and cochleamycin A are also discussed. [reaction: see text]

Publication types

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

MeSH terms

Acylation
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Molecular Structure
Naphthalenes / chemistry*
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry

Substances

Antineoplastic Agents
FR 182877
Naphthalenes
Polycyclic Compounds
allenolic acid

Grants and funding

CA 85526/CA/NCI NIH HHS/United States