CaltechAUTHORS
  A Caltech Library Service

Enantioselective Total Synthesis of (+)-Salvileucalin B

Levin, Sergiy and Nani, Roger R. and Reisman, Sarah E. (2011) Enantioselective Total Synthesis of (+)-Salvileucalin B. Journal of the American Chemical Society, 133 (4). pp. 774-776. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20110321-160052573

[img]
Preview
PDF - Supplemental Material
See Usage Policy.

835Kb
[img]
Preview
PDF - Supplemental Material
See Usage Policy.

2512Kb
[img] Crystallographic Info File (CIF) - Supplemental Material
See Usage Policy.

22Kb

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20110321-160052573

Abstract

An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported. Key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized norcaradiene intermediate.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja110192b DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja110192bPublisherArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2010 American Chemical Society. Received: November 12, 2010. Article ASAP December 21, 2010. Published In Issue February 02, 2011. We thank Drs. Michael Day and Larry Henling for X-ray crystallographic structural determination and Dr. Scott Virgil for insightful discussions. We thank Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE-0639094, CHE-0541745). Ms. Kendra Joseph is acknowledged for assistance in the preparation of alkyne 9. Financial support from the California Institute of Technology is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSFCHE-0639094
NSFCHE-0541745
CaltechUNSPECIFIED
Issue or Number:4
Record Number:CaltechAUTHORS:20110321-160052573
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110321-160052573
Official Citation:Enantioselective Total Synthesis of (+)-Salvileucalin B Sergiy Levin, Roger R. Nani, Sarah E. Reisman Journal of the American Chemical Society 2011 133 (4), 774-776
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23020
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:22 Mar 2011 21:48
Last Modified:03 Oct 2019 02:42

Repository Staff Only: item control page