ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Formal Total Synthesis of (±)-Isocomen by Application of the α-Alkinon CyclizationA total synthesis of the racemic form of the sesquiterpene isocomene (A) was accomplished by application of the cyclopentenone anellation B→D (Scheme 1) which includes the α-alkynone cyclization C→D, a gas-phase flow thermolytic process. Starting with the known product 2 (Scheme 3) of the anellation B→D, the elaboration of ring C of A proceeded in 9 steps to the α-alkynone 16 (Scheme 5) which was cyclized at 540° selectively to give the angularly fused triquinane 4 (77%). A two-step procedure then led to 5 (Scheme 6), a last but one intermediate in a known total synthesis of (±)-A. The conversion of 16 to 4 also demonstrated the compatibility of an acetoxy function with the anellation sequence B→D.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19860690316
