Abstract
An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)-(+)-carvone in 21 steps and with an overall yield of 12%. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a 1,3-sigmatropic rearrangement and an intramolecular Diels-Alder reaction as the key steps.
| Original language | English |
|---|---|
| Pages (from-to) | 5489-5500 |
| Number of pages | 12 |
| Journal | Chemistry - A European Journal |
| Volume | 9 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - 2003 Nov 21 |
| Externally published | Yes |
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Keywords
- Antitumor agents
- Lactones
- Terpenoids
- Total synthesis
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Studies towards Simalikalactone D and Quassimarin : Construction of an Advanced Pentacyclic Intermediate. / Shing, Tony Kung Ming; Zhu, Xue Y.; Yeung, Yeung Y.
In: Chemistry - A European Journal, Vol. 9, No. 22, 21.11.2003, p. 5489-5500.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Studies towards Simalikalactone D and Quassimarin
T2 - Construction of an Advanced Pentacyclic Intermediate
AU - Shing, Tony Kung Ming
AU - Zhu, Xue Y.
AU - Yeung, Yeung Y.
PY - 2003/11/21
Y1 - 2003/11/21
N2 - An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)-(+)-carvone in 21 steps and with an overall yield of 12%. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a 1,3-sigmatropic rearrangement and an intramolecular Diels-Alder reaction as the key steps.
AB - An advanced pentacyclic intermediate, amenable to further elaboration into the target molecules simalikalactone D and quassimarin, has been synthesized from (S)-(+)-carvone in 21 steps and with an overall yield of 12%. The synthesis is efficient, stereocontrolled, enantiospecific, and chirality productive, creating eight new chiral centres in pentacycle, and should provide opportunities for rapid access to simalikalactone D analogues and other bioactive quassinoids. The reaction sequence involves a regioselective bishydroxylmethylation, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a 1,3-sigmatropic rearrangement and an intramolecular Diels-Alder reaction as the key steps.
KW - Antitumor agents
KW - Lactones
KW - Terpenoids
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=0347089002&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0347089002&partnerID=8YFLogxK
U2 - 10.1002/chem.200305158
DO - 10.1002/chem.200305158
M3 - Article
C2 - 14639632
AN - SCOPUS:0347089002
VL - 9
SP - 5489
EP - 5500
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 22
ER -