A short and efficient synthesis of (+)-totarol

Victor Rogachev, Thorsten Löhl, Thomas Markert, Peter Metz

Research output: Contribution to journalArticle

5 Citations (Scopus)

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 languageEnglish
Pages (from-to)172-180
Number of pages9
JournalArkivoc
Volume2012
Issue number3
DOIs
Publication statusPublished - 23 Jan 2012
Externally publishedYes

Fingerprint

Diterpenes
Alkylation
Condensation
manool
totarol
sclareol
3-hydroxybutanal

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

A short and efficient synthesis of (+)-totarol. / Rogachev, Victor; Löhl, Thorsten; Markert, Thomas; Metz, Peter.

In: Arkivoc, Vol. 2012, No. 3, 23.01.2012, p. 172-180.

Research output: Contribution to journalArticle

Rogachev, V, Löhl, T, Markert, T & Metz, P 2012, 'A short and efficient synthesis of (+)-totarol', Arkivoc, vol. 2012, no. 3, pp. 172-180. https://doi.org/10.3998/ark.5550190.0013.313
Rogachev V, Löhl T, Markert T, Metz P. A short and efficient synthesis of (+)-totarol. Arkivoc. 2012 Jan 23;2012(3):172-180. https://doi.org/10.3998/ark.5550190.0013.313
Rogachev, Victor ; Löhl, Thorsten ; Markert, Thomas ; Metz, Peter. / A short and efficient synthesis of (+)-totarol. In: Arkivoc. 2012 ; Vol. 2012, No. 3. pp. 172-180.
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