Format

Send to

Choose Destination
Org Lett. 2015 Jul 2;17(13):3358-61. doi: 10.1021/acs.orglett.5b01629. Epub 2015 Jun 12.

Total Synthesis of Oridamycins A and B.

Author information

1
Tri-Institutional PhD Program in Chemical Biology, Laboratory for Bioorganic Chemistry, Memorial Sloan Kettering Cancer Center, Sloan Kettering Institute, 1275 York Avenue, New York, New York 10065, United States.

Abstract

The total synthesis of both oridamycin A and oridamycin B was accomplished starting from a common synthetic intermediate readily prepared from geranyl acetate. The sequence utilizes an oxidative radical cyclization to construct the trans-decalin ring system, setting three of four contiguous stereocenters in one operation. The carbazole nucleus was forged through a one-pot process entailing acid-promoted dehydration followed by 6π-electrocyclization/aromatization.

PMID:
26069989
PMCID:
PMC5606188
DOI:
10.1021/acs.orglett.5b01629
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center