Published September 17, 2012
| Supplemental Material + Accepted Version
Journal Article
Open
Enantioselective Total Synthesis of the Reported Structures of (−)-9-epi-Presilphiperfolan-1-ol and (−)-Presilphiperfolan-1-ol: Structural Confirmation and Reassignment and Biosynthetic Insights
- Creators
- Hong, Allen Y.
-
Stoltz, Brian M.
Abstract
The first total synthesis of the reported structures of 9-epi-presilphiperfolan-1-ol and presilphiperfolan-1-ol has been achieved. Key steps are a catalytic asymmetric alkylation of a novel diene-containing electrophile followed by a two-carbon ring contraction and an intramolecular Diels–Alder cycloaddition to form the stereochemically dense tricyclic core. The synthetic work has resulted in the structural revision of presilphiperfolan-1-ol (see scheme).
Additional Information
Copyright © 2012 WILEY-VCH. Received: July 4, 2012. Published online: August 22, 2012. In memory of Michael W. Day. The authors thank NIH-NIGMS (R01GM080269-01), Roche, Abbott Laboratories, Amgen, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for awards and financial support. Prof. Suzana G. Leitão (Universidade Federale do Rio de Janeiro) generously provided NMR spectra for natural 2. Dr. Lawrence Henling is gratefully acknowledged for X-ray crystallographic structure determination. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech (CHE-0639094). Prof. Sarah Reisman, Dr. Scott Virgil, Dr. Douglas C. Behenna, Robert J. Ely and Fang Gao (Boston College), and Jessica Y. Wu (Harvard University) are acknowledged for helpful discussions and suggestions. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR assistance.Errata
Corrigendum: Corrigendum: Enantioselective Total Synthesis of the Reported Structures of (−)-9-epi-Presilphiperfolan-1-ol and (−)-Presilphiperfolan-1-ol: Structural Confirmation and Reassignment and Biosynthetic Insights Vol. 52, Issue 8, 2147Attached Files
Accepted Version - nihms-412653.pdf
Supplemental Material - anie_201205276_sm_miscellaneous_information.pdf
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anie_201205276_sm_miscellaneous_information.pdf
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Additional details
- PMCID
- PMC3517068
- Eprint ID
- 52975
- Resolver ID
- CaltechAUTHORS:20141217-142148376
- R01GM080269-01
- NIH
- Roche
- Abbott Laboratories
- Amgen
- Boehringer Ingelheim
- Gordon and Betty Moore Foundation
- Caltech
- CHE-0639094
- NSF
- Created
-
2014-12-17Created from EPrint's datestamp field
- Updated
-
2023-06-01Created from EPrint's last_modified field