Iodo-cyclizations: novel strategy for the total syntheses of polyrhacitide A and epi-cryptocaryolone

Debendra K Mohapatra; Eswar Bhimireddy; P Sivarama Krishnarao; Pragna P Das; J S Yadav

doi:10.1021/ol1029854

Iodo-cyclizations: novel strategy for the total syntheses of polyrhacitide A and epi-cryptocaryolone

Org Lett. 2011 Feb 18;13(4):744-7. doi: 10.1021/ol1029854. Epub 2011 Jan 7.

Authors

Debendra K Mohapatra¹, Eswar Bhimireddy, P Sivarama Krishnarao, Pragna P Das, J S Yadav

Affiliation

¹ Organic Chemistry Division-I, Indian Institute of Chemical Technology (CSIR), Hyderabad 500 607, India. mohapatra@iict.res.in

PMID: 21214256
DOI: 10.1021/ol1029854

Abstract

Highly stereoselective total syntheses of polyrhacitide A and epi-cryptocaryolone have been achieved in 11 steps with high overall yield of 24% and 28%, respectively, following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4-dihydropyrans. In this report, the versatility of iodo-cyclization for the total syntheses of polyrhacitide A and epi-cryptocaryolone is demonstrated.

Publication types

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

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Catalysis
Cyclization
Iodine / chemistry*
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure
Pyrans / chemical synthesis
Pyrans / chemistry*
Pyrones / chemical synthesis*
Pyrones / chemistry
Stereoisomerism

Substances

Bridged Bicyclo Compounds, Heterocyclic
Lactones
Pyrans
Pyrones
cryptocaryolone
polyrhacitide A
3,4-dihydropyran
Iodine