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Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions

Kim, Yuntae and Singer, Robert A. and Carreira, Erick M. (1998) Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions. Angewandte Chemie International Edition, 37 (9). pp. 1261-1263. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20180507-142321043

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Abstract

A highly convergent total synthesis of macrolactin A (1) utilizes modern asymmetric catalytic C–C coupling methods. The longest linear sequence in the route is 16 steps with an average yield of 86% per step. This total synthesis is valuable, because 1, which has been shown to possess activity against HIV, is not readily accessible from its natural source, a taxonomically unclassified deep‐sea bacterium.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/(SICI)1521-3773(19980518)37:9<1261::AID-ANIE1261>3.0.CO;2-2DOIArticle
ORCID:
AuthorORCID
Carreira, Erick M.0000-0003-1472-490X
Additional Information:© 1998 Wiley‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany. Issue Online: 17 December 1998; Version of Record online: 17 December 1998; Manuscript received: 17 November 1997. This work was supported by the National Science Foundation and the National Institutes of Health.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
NIHUNSPECIFIED
Subject Keywords:Aldol reactions; Asymmetric catalysis; Macrolactin A; Natural products; Palladium; Total synthesis
Issue or Number:9
Record Number:CaltechAUTHORS:20180507-142321043
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180507-142321043
Official Citation:Kim, Y. , Singer, R. A. and Carreira, E. M. (1998), Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions. Angewandte Chemie International Edition, 37: 1261-1263. doi:10.1002/(SICI)1521-3773(19980518)37:9<1261::AID-ANIE1261>3.0.CO;2-2
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86268
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 May 2018 21:43
Last Modified:09 Mar 2020 13:18

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