Cart
Letter
Enantioselective Total Synthesis of Peloruside A: A Potent Microtubule Stabilizer
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
An enantioselective total synthesis of (+)-peloruside A (1) is described. Peloruside A (1) is a potent microtubule stabilizer with significant clinical potential. The synthesis is convergent and involves the assembly of C1−C10 segment 2 and C11−C24 segment 3 by a novel aldol protocol followed by Yamaguchi macrolactonization of the resulting seco-acid, selective methylation of hemi-ketal and removal of the protecting groups to peloruside A.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 11 ACS Journal articles (5 most recent appear below).
Rapid Access to Conformational Analogues of (+)-Peloruside A
Zhiming Zhao and Richard E. TaylorOrganic Letters2012 14 (3), 669-671Rapid Access to Conformational Analogues of (+)-Peloruside A
Zhiming Zhao and Richard E. TaylorOrganic Letters2012 14 (3), 669-671An efficient synthetic strategy for rapid access to analogues of peloruside A has been demonstrated. The synthetic route was highlighted by a simple esterification-based fragment coupling and a late stage ring-closing metathesis reaction. This convergent ...
Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
Jeffrey A. Gazaille, Joseph A. Abramite, and Tarek SammakiaOrganic Letters2012 14 (1), 178-181Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction
Jeffrey A. Gazaille, Joseph A. Abramite, and Tarek SammakiaOrganic Letters2012 14 (1), 178-181The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19 and proceeds in high yield and good levels of ...
Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine
Arun K. GhoshThe Journal of Organic Chemistry2010 75 (23), 7967-7989Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine
Arun K. GhoshThe Journal of Organic Chemistry2010 75 (23), 7967-7989In this Perspective, I outline my group’s research involving the chemical syntheses of medicinally important natural products, exploration of their bioactivity, and the development of new asymmetric carbon−carbon bond-forming reactions. This paper also ...
The Assembly-Inducing Laulimalide/Peloruside A Binding Site on Tubulin: Molecular Modeling and Biochemical Studies with [3H]Peloruside A
Tam Luong Nguyen, Xiaoming Xu, Rick Gussio, Arun K. Ghosh, and Ernest HamelJournal of Chemical Information and Modeling2010 50 (11), 2019-2028The Assembly-Inducing Laulimalide/Peloruside A Binding Site on Tubulin: Molecular Modeling and Biochemical Studies with [3H]Peloruside A
Tam Luong Nguyen, Xiaoming Xu, Rick Gussio, Arun K. Ghosh, and Ernest HamelJournal of Chemical Information and Modeling2010 50 (11), 2019-2028We used synthetic peloruside A for the commercial preparation of [3H]peloruside A. The radiolabeled compound bound to preformed tubulin polymer in amounts stoichiometric with the polymer’s tubulin content, with an apparent Kd value of 0.35 μM. A less ...
Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and -1b
Arun K. Ghosh and Hao YuanOrganic Letters2010 12 (14), 3120-3123Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and -1b
Arun K. Ghosh and Hao YuanOrganic Letters2010 12 (14), 3120-3123Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue March 06, 2008
- Received December 22, 2007
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
