Total Synthesis of the Marine Phosphomacrolide, (-)-Enigmazole A, Exploiting Multicomponent Type I Anion Relay Chemistry (ARC) in Conjunction with a Late-Stage Petasis-Ferrier Union/Rearrangement

Yanran Ai; Mariya V Kozytska; Yike Zou; Anton S Khartulyari; William A Maio; Amos B Smith 3rd

doi:10.1021/acs.joc.8b00899

Total Synthesis of the Marine Phosphomacrolide, (-)-Enigmazole A, Exploiting Multicomponent Type I Anion Relay Chemistry (ARC) in Conjunction with a Late-Stage Petasis-Ferrier Union/Rearrangement

J Org Chem. 2018 Jun 1;83(11):6110-6126. doi: 10.1021/acs.joc.8b00899. Epub 2018 May 22.

Authors

Yanran Ai¹, Mariya V Kozytska¹, Yike Zou¹, Anton S Khartulyari¹, William A Maio¹, Amos B Smith 3rd¹

Affiliation

¹ Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center , University of Pennsylvania , Philadelphia , Pennsylvania 19104 , United States.

Abstract

An effective late-stage large-fragment union/rearrangement exploiting the Petasis-Ferrier protocol, in conjunction with multicomponent Type I Anion Relay Chemistry (ARC) to access advanced intermediates, permits completion of a convergent, stereocontrolled total synthesis of the architecturally complex phosphomacrolide (-)-enigmazole A (1).

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Cyclization
Hydrogen-Ion Concentration
Macrolides / chemical synthesis*
Molecular Structure
Organophosphorus Compounds / chemical synthesis*
Oxazoles / chemical synthesis*
Oxidation-Reduction
Stereoisomerism
Temperature

Substances

Macrolides
Organophosphorus Compounds
Oxazoles
enigmazole A

Grants and funding

R01 CA019033/CA/NCI NIH HHS/United States