A short and efficient synthesis of (+)-totarol

Abstract

A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1.

Original language	English
Pages (from-to)	172-180
Number of pages	9
Journal	Arkivoc
Volume	2012
Issue number	3
DOIs	https://doi.org/10.3998/ark.5550190.0013.313
Publication status	Published - 23 Jan 2012
Externally published	Yes

Keywords

Antibacterials
Diterpenes
Manool
Natural products
Sclareol
Semisynthesis

ASJC Scopus subject areas

Organic Chemistry

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10.3998/ark.5550190.0013.313

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title = "A short and efficient synthesis of (+)-totarol",

abstract = "A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1.",

keywords = "Antibacterials, Diterpenes, Manool, Natural products, Sclareol, Semisynthesis",

author = "Victor Rogachev and Thorsten L{\"o}hl and Thomas Markert and Peter Metz",

year = "2012",

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doi = "10.3998/ark.5550190.0013.313",

language = "English",

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T1 - A short and efficient synthesis of (+)-totarol

AU - Rogachev, Victor

AU - Löhl, Thorsten

AU - Markert, Thomas

AU - Metz, Peter

PY - 2012/1/23

Y1 - 2012/1/23

N2 - A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1.

AB - A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1.

KW - Antibacterials

KW - Diterpenes

KW - Manool

KW - Natural products

KW - Sclareol

KW - Semisynthesis

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DO - 10.3998/ark.5550190.0013.313

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EP - 180

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