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Merck

Total synthesis of alotaketal A.

Organic letters (2012-10-26)
Mengyang Xuan, Ian Paterson, Stephen M Dalby
PMID23094646
ABSTRACT

The total synthesis of the cAMP signaling pathway activator (-)-alotaketal A is reported. A convergent approach to the unusual alotane sesterterpenoid skeleton was employed, exploiting a remarkable LiDBB-mediated coupling of an (R)-carvone-derived δ-lactone with an allyl bromide side chain, followed by spiroacetalization.

MATERIALS
Product Number
Brand
Product Description
W224901
Sigma-Aldrich
L-Carvone, ≥97%, FCC, FG
W224908
Sigma-Aldrich
L-Carvone, natural, 99%, FG
124931
Sigma-Aldrich
(R)-(−)-Carvone, 98%
W224928
Sigma-Aldrich
D-Carvone, ≥96%, FG
22060
Supelco
(−)-Carvone, analytical standard
22070
Supelco
(+)-Carvone, analytical standard
435759
Sigma-Aldrich
(S)-(+)-Carvone, 96%
79245
Supelco
(+)-Carvone, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland