Chemistry - A European Journal, volume 21, issue 36, pages 12804-12808

Enantioselective Synthesis of Lepadins A-D from a Phenylglycinol-Derived Hydroquinolone Lactam

Mercedes Amat ¹

Alexandre Pinto ¹

Rosa Griera ¹

Joan Bosch ¹

Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain), Fax: (+34) 93‐402‐45‐39 http://www.ub.edu/sintefarma/ |

Publication type: Journal Article

Publication date: 2015-07-21

Wiley

Journal: Chemistry - A European Journal

scimago Q1

SJR: 1.058

CiteScore: 7.9

Impact factor: 3.9

ISSN: 09476539, 15213765

DOI: 10.1002/chem.201501909

Copy DOI

PubMed ID: 26202059

General Chemistry

Catalysis

Organic Chemistry

Abstract

The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.

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Wiley	Wiley, 2, 11.11% Wiley 2 publications, 11.11%
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Publisher

Wiley

Journal

Chemistry - A European Journal

scimago Q1

SJR

1.058

CiteScore

7.9

Impact factor

3.9

ISSN

09476539 (Print)

15213765 (Electronic)

Enantioselective Synthesis of Lepadins A-D from a Phenylglycinol-Derived Hydroquinolone Lactam

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