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Total synthesis of (-)-callystatin A.
Org Lett. 2004 Sep 02; 6(18):3203-6.OL

Abstract

[reaction: see text] A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin.

Authors+Show Affiliations

Langille NF
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek JS
No affiliation info available

MeSH

AlkenesAnimalsCatalysisFatty Acids, UnsaturatedMolecular StructurePoriferaStereoisomerismTin

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15330623

Citation

Langille, Neil F., and James S. Panek. "Total Synthesis of (-)-callystatin A." Organic Letters, vol. 6, no. 18, 2004, pp. 3203-6.
Langille NF, Panek JS. Total synthesis of (-)-callystatin A. Org Lett. 2004;6(18):3203-6.
Langille, N. F., & Panek, J. S. (2004). Total synthesis of (-)-callystatin A. Organic Letters, 6(18), 3203-6.
Langille NF, Panek JS. Total Synthesis of (-)-callystatin A. Org Lett. 2004 Sep 2;6(18):3203-6. PubMed PMID: 15330623.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (-)-callystatin A. AU - Langille,Neil F, AU - Panek,James S, PY - 2004/8/28/pubmed PY - 2005/9/22/medline PY - 2004/8/28/entrez SP - 3203 EP - 6 JF - Organic letters JO - Org Lett VL - 6 IS - 18 N2 - [reaction: see text] A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15330623/Total_synthesis_of_____callystatin_A_ DB - PRIME DP - Unbound Medicine ER -