Highly efficient synthesis of the natural spiro-terpenoid (±)-andirolactone

A. Orduna; L. G. Zepeda; J. Tamariz

doi:10.1055/s-1993-25866

Highly efficient synthesis of the natural spiro-terpenoid (±)-andirolactone

A. Orduna, L. G. Zepeda, J. Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

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

43 Scopus citations

Abstract

A synthesis of the natural terpenoid sporilactone (±)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl-4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of olefin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46% overall yield.

Original language	English
Pages (from-to)	375-377
Number of pages	3
Journal	Synthesis (Germany)
Issue number	4
DOIs	https://doi.org/10.1055/s-1993-25866
State	Published - 1993

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title = "Highly efficient synthesis of the natural spiro-terpenoid (±)-andirolactone",

abstract = "A synthesis of the natural terpenoid sporilactone (±)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl-4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of olefin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46% overall yield.",

author = "A. Orduna and Zepeda, {L. G.} and J. Tamariz",

year = "1993",

doi = "10.1055/s-1993-25866",

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journal = "Synthesis (Germany)",

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T1 - Highly efficient synthesis of the natural spiro-terpenoid (±)-andirolactone

AU - Orduna, A.

AU - Zepeda, L. G.

AU - Tamariz, J.

PY - 1993

Y1 - 1993

N2 - A synthesis of the natural terpenoid sporilactone (±)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl-4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of olefin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46% overall yield.

AB - A synthesis of the natural terpenoid sporilactone (±)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl-4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of olefin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46% overall yield.

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U2 - 10.1055/s-1993-25866

DO - 10.1055/s-1993-25866

M3 - Artículo

SN - 0039-7881

SP - 375

EP - 377

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 4

ER -

Highly efficient synthesis of the natural spiro-terpenoid (±)-andirolactone

Abstract

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