Convolutamydine A: the First Authenticated Absolute Configuration and Enantioselective Synthesis

G CRAVOTTO; Giovanni Battista GIOVENZANA; G PALMISANO; A PENONI; T PILATI; M SISTI; F. STAZI

doi:10.1016/j.tetasy.2006.11.021

Convolutamydine A: the First Authenticated Absolute Configuration and Enantioselective Synthesis

G CRAVOTTO
, Giovanni Battista GIOVENZANA
, G PALMISANO
, A PENONI
, T PILATI
, M SISTI
, F. STAZI

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed π-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography.

Lingua originale	Inglese
pagine (da-a)	3070-3074
Numero di pagine	5
Rivista	TETRAHEDRON-ASYMMETRY
Volume	17
Numero di pubblicazione	22
DOI	https://doi.org/10.1016/j.tetasy.2006.11.021
Stato di pubblicazione	Pubblicato - 2006

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10.1016/j.tetasy.2006.11.021

http://hdl.handle.net/11579/19362

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@article{25febf60f9d8422e9da34747e9946709,

title = "Convolutamydine A: the First Authenticated Absolute Configuration and Enantioselective Synthesis",

abstract = "The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed π-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography.",

author = "G CRAVOTTO and GIOVENZANA, \{Giovanni Battista\} and G PALMISANO and A PENONI and T PILATI and M SISTI and F. STAZI",

note = "Funding Information: Financial support from Regione Piemonte (Ricerca Scientifica Applicata 2004) is gratefully acknowledged.",

year = "2006",

doi = "10.1016/j.tetasy.2006.11.021",

language = "English",

volume = "17",

pages = "3070--3074",

journal = "TETRAHEDRON-ASYMMETRY",

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number = "22",

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TY - JOUR

T1 - Convolutamydine A: the First Authenticated Absolute Configuration and Enantioselective Synthesis

AU - CRAVOTTO, G

AU - GIOVENZANA, Giovanni Battista

AU - PALMISANO, G

AU - PENONI, A

AU - PILATI, T

AU - SISTI, M

AU - STAZI, F.

N1 - Funding Information: Financial support from Regione Piemonte (Ricerca Scientifica Applicata 2004) is gratefully acknowledged.

PY - 2006

Y1 - 2006

N2 - The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed π-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography.

AB - The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed π-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography.

UR - https://iris.uniupo.it/handle/11579/19362

U2 - 10.1016/j.tetasy.2006.11.021

DO - 10.1016/j.tetasy.2006.11.021

M3 - Article

SN - 0957-4166

VL - 17

SP - 3070

EP - 3074

JO - TETRAHEDRON-ASYMMETRY

JF - TETRAHEDRON-ASYMMETRY

IS - 22

ER -

Convolutamydine A: the First Authenticated Absolute Configuration and Enantioselective Synthesis

Abstract

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