A short and efficient synthesis of (+)-totarol

Victor Rogachev, Thorsten Löhl, Thomas Markert, Peter Metz

Research output: Contribution to journal › Article

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

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Keywords

Antibacterials
Diterpenes
Manool
Natural products
Sclareol
Semisynthesis

ASJC Scopus subject areas

Organic Chemistry

Cite this

Rogachev, V., Löhl, T., Markert, T., & Metz, P. (2012). A short and efficient synthesis of (+)-totarol. Arkivoc, 2012(3), 172-180. https://doi.org/10.3998/ark.5550190.0013.313

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10.3998/ark.5550190.0013.313