CaltechAUTHORS
  A Caltech Library Service

Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine

Liu, Qi and Ferreira, Eric M. and Stoltz, Brian M. (2007) Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine. Journal of Organic Chemistry, 72 (19). pp. 7352-7358. ISSN 0022-3263. doi:10.1021/jo0710883. https://resolver.caltech.edu/CaltechAUTHORS:20170215-155814896

[img] PDF - Supplemental Material
See Usage Policy.

440kB
[img] PDF - Supplemental Material
See Usage Policy.

5MB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20170215-155814896

Abstract

A concise route toward the syntheses of (−)-drupacine and (+)- and (−)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an important spirocyclic amine intermediate. A dynamic β-elimination/conjugate addition process was strategically applied to complete the first asymmetric total synthesis of (−)-drupacine.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo0710883DOIArticle
http://pubs.acs.org/doi/suppl/10.1021/jo0710883PublisherSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2007 American Chemical Society. Received June 8, 2007; Publication Date (Web): August 18, 2007. We thank the NIH-NIGMS (R01 GM65961-01), Bristol-Myers Squibb Co. (graduate fellowship to E.M.F.), the NSF (graduate fellowship to E.M.F.), the Dreyfus Foundation, Merck Research Laboratories, Research Corporation, Abbott Laboratories, Pfizer, Amgen, GlaxoSmithKline, Lilly, and Johnson and Johnson for generous financial support. We are grateful to Ernie Cruz, Sandy Ma, and John Enquist for experimental assistance.
Funders:
Funding AgencyGrant Number
NIHR01GM65961-01
Bristol-Myers Squibb CompanyUNSPECIFIED
NSF Graduate Research FellowshipUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Research CorporationUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
PfizerUNSPECIFIED
AmgenUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Eli LillyUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
Issue or Number:19
DOI:10.1021/jo0710883
Record Number:CaltechAUTHORS:20170215-155814896
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170215-155814896
Official Citation:Convergency and Divergency as Strategic Elements in Total Synthesis:  The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine Qi Liu, Eric M. Ferreira, and Brian M. Stoltz The Journal of Organic Chemistry 2007 72 (19), 7352-7358 DOI: 10.1021/jo0710883
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74349
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Feb 2017 00:23
Last Modified:11 Nov 2021 05:26

Repository Staff Only: item control page