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 | |
| 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
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 journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=84875541454&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84875541454&partnerID=8YFLogxK
U2 - 10.3998/ark.5550190.0013.313
DO - 10.3998/ark.5550190.0013.313
M3 - Article
VL - 2012
SP - 172
EP - 180
JO - Arkivoc
JF - Arkivoc
SN - 1424-6376
IS - 3
ER -