Unexpected oxidation of ortho-phenol groups of carnosol with m-chloroperbenzoic acid

Joaquín G. Marrero; Lucía San Andrés Tejera; Javier G. Luis; Matías L. Rodríguez

doi:10.1055/s-2002-33513

Unexpected oxidation of ortho-phenol groups of carnosol with m-chloroperbenzoic acid

Joaquín G. Marrero, Lucía San Andrés Tejera, Javier G. Luis, Matías L. Rodríguez

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

8 Citas (Scopus)

Resumen

The oxidation reaction of carnosol (2) with m-chloroperbenzoic acid and sodium bicarbonate in dichloromethane gave an abietane diterpene (3) with an anhydride function on C ring. The conversion can be rationalized by a Baeyer-Villiger reaction from the initially generated ortho-quinone. The structure of this anhydride was confirmed by spectroscopic and X-ray crystallographic analysis. This reaction could be an important key step towards the synthesis of natural products such us drimane sesquiterpenes.

Idioma original	Inglés
Páginas (desde-hasta)	1517-1519
Número de páginas	3
Publicación	Synlett
N.º	9
DOI	https://doi.org/10.1055/s-2002-33513
Estado	Publicada - 2002
Publicado de forma externa	Sí

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title = "Unexpected oxidation of ortho-phenol groups of carnosol with m-chloroperbenzoic acid",

abstract = "The oxidation reaction of carnosol (2) with m-chloroperbenzoic acid and sodium bicarbonate in dichloromethane gave an abietane diterpene (3) with an anhydride function on C ring. The conversion can be rationalized by a Baeyer-Villiger reaction from the initially generated ortho-quinone. The structure of this anhydride was confirmed by spectroscopic and X-ray crystallographic analysis. This reaction could be an important key step towards the synthesis of natural products such us drimane sesquiterpenes.",

keywords = "Abietatriene diterpenes, Natural products, Oxidation, Rearrangement, Ring expansion",

author = "Marrero, {Joaqu{\'i}n G.} and {San Andr{\'e}s Tejera}, Luc{\'i}a and Luis, {Javier G.} and Rodr{\'i}guez, {Mat{\'i}as L.}",

year = "2002",

doi = "10.1055/s-2002-33513",

language = "Ingl{\'e}s",

pages = "1517--1519",

journal = "Synlett",

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TY - JOUR

T1 - Unexpected oxidation of ortho-phenol groups of carnosol with m-chloroperbenzoic acid

AU - Marrero, Joaquín G.

AU - San Andrés Tejera, Lucía

AU - Luis, Javier G.

AU - Rodríguez, Matías L.

PY - 2002

Y1 - 2002

N2 - The oxidation reaction of carnosol (2) with m-chloroperbenzoic acid and sodium bicarbonate in dichloromethane gave an abietane diterpene (3) with an anhydride function on C ring. The conversion can be rationalized by a Baeyer-Villiger reaction from the initially generated ortho-quinone. The structure of this anhydride was confirmed by spectroscopic and X-ray crystallographic analysis. This reaction could be an important key step towards the synthesis of natural products such us drimane sesquiterpenes.

AB - The oxidation reaction of carnosol (2) with m-chloroperbenzoic acid and sodium bicarbonate in dichloromethane gave an abietane diterpene (3) with an anhydride function on C ring. The conversion can be rationalized by a Baeyer-Villiger reaction from the initially generated ortho-quinone. The structure of this anhydride was confirmed by spectroscopic and X-ray crystallographic analysis. This reaction could be an important key step towards the synthesis of natural products such us drimane sesquiterpenes.

KW - Abietatriene diterpenes

KW - Natural products

KW - Oxidation

KW - Rearrangement

KW - Ring expansion

UR - http://www.scopus.com/inward/record.url?scp=0036375550&partnerID=8YFLogxK

U2 - 10.1055/s-2002-33513

DO - 10.1055/s-2002-33513

M3 - Artículo

SN - 0936-5214

SP - 1517

EP - 1519

JO - Synlett

JF - Synlett

IS - 9

ER -

Unexpected oxidation of ortho-phenol groups of carnosol with m-chloroperbenzoic acid

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