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

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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.

Original language	English
Pages (from-to)	1517-1519
Number of pages	3
Journal	Synlett
Issue number	9
DOIs	https://doi.org/10.1055/s-2002-33513
State	Published - 2002
Externally published	Yes

Keywords

Abietatriene diterpenes
Natural products
Oxidation
Rearrangement
Ring expansion

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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.",

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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.}",

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

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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

Abstract

Keywords

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