SYNTHESIS OF SPIRO[4.5]DECAN-1-ONES - A FORMAL SYNTHESIS OF ACORADIENES AND RELATED SESQUITERPENES VIA RHODIUM-CATALYZED CLAISEN REARRANGEMENT HYDROACYLATION/

Authors
SATTELKAU T HOLLMANN C EILBRACHT P
Citation
T. Sattelkau et al., SYNTHESIS OF SPIRO[4.5]DECAN-1-ONES - A FORMAL SYNTHESIS OF ACORADIENES AND RELATED SESQUITERPENES VIA RHODIUM-CATALYZED CLAISEN REARRANGEMENT HYDROACYLATION/, Synlett, (12), 1996, pp. 1221
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
12
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):12<1221:SOS-AF>2.0.ZU;2-X
Abstract
A novel procedure for the synthesis of spiro[4.5]decan-1-ones starting from commercially available substances is described. The key-step is a one-pot combination of Claisen rearrangement of allyl vinyl ethers f ollowed by an. intramolecular hydroacylation(1) catalysed by RhCl(cod) (dppe).(2) The intermediate pent-4-enals generated by the initial [3.3 ] sigmatropic rearrangement exhibit substitution patterns which have p reviously been described as unsuitable for the rhodium catalysed intra molecular hydroacylation.(3,4) This procedure allows the synthesis of ketone 2, a key intermediate in the total synthesis of acoradienes and acorones.(5)