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Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline

Author

Amat Tusón, Mercedes

Ramos, Carlos

Pérez Bosch, Maria

Molins i Grau, Elies

Florindo, Pedro

Santos, Maria M. M.

Bosch Cartes, Joan

Publication date

2013-04-30T10:52:01Z

2014-03-07T23:02:13Z

2013-03-07

2013-04-29T15:13:30Z

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Abstract

Starting from (S)-tryptophanol, a formal synthesis of ent-rhyncho-phylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.

Document Type

Article

Accepted version

Language

English

Subjects and keywords

Alcaloides; Síntesi asimètrica; Estereoquímica; Alkaloids; Asymmetric synthesis; Stereochemistry

Publisher

Royal Society of Chemistry

Related items

Versió postprint del document publicat a: http://dx.doi.org/10.1039/c2cc38540f

Chemical Communications, 2013, vol. 49, num. 19, p. 1954-1956

http://dx.doi.org/10.1039/c2cc38540f

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Rights

(c) Amat Tusón, Mercedes et al., 2013

This item appears in the following Collection(s)

Farmacologia, Toxicologia i Química Terapèutica [675]

ISGlobal - Institut de Salut Global de Barcelona [60793]