First synthesis and structural elucidation of (-)-presphaerene.

Journal Article (Journal Article)

The first total synthesis of (-)-presphaerene (1) was achieved from (R)-glyceraldehyde 9 in 19 steps, demonstrating the novel "folding and allylic strain-controlled" intramolecular ester enolate S(N)2' alkylation strategy could be extended to the stereoselective synthesis of cyclopentanoid natural products. The present study also established the relative and absolute stereochemistry of 1, and the absolute structures of co-occurring sphaeroanes from the red alga Sphaerococcus coronopifolius.

Full Text

Duke Authors

Cited Authors

  • Lee, J; Hong, J

Published Date

  • September 2004

Published In

Volume / Issue

  • 69 / 19

Start / End Page

  • 6433 - 6440

PubMed ID

  • 15357605

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo049351c


  • eng