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Beilstein J. Org. Chem. 2019, 15, 858–862, doi:10.3762/bjoc.15.83
Graphical Abstract
Figure 1: Structures of the sesquiterpene (−)-isoguaiene (1) and the trisnorsesquiterpene clavukerin A (2).
Scheme 1: Retrosynthetic analysis for (−)-isoguaiene (1).
Scheme 2: Synthesis of 1 by relay metathesis of trienyne 3. a) HC(OMe)3, 4 mol % LiBF4, MeOH, reflux, 80%; b)...
Scheme 3: Attempted preparation of 1 by domino metathesis of enediyne 7. a) (i) O3, CH2Cl2, MeOH, pyridine, −...
Scheme 4: Conversion of 28 to 1 by relay metathesis of dienediyne 8. a) (i) 21, THF, rt to reflux, (ii) BuLi,...
Beilstein J. Org. Chem. 2013, 9, 2028–2032, doi:10.3762/bjoc.9.239
Figure 1: Structure of the guaiane (−)-oxyphyllol (1).
Scheme 1: Retrosynthetic analysis for (−)-oxyphyllol (1) and structures of the guaiane sesquiterpenes (+)-ori...
Scheme 2: Attempted selective deoxygenation of diol 7. a) 1 mol % K2OsO4, NMO, acetone, water, THF, rt, 97%, ...
Scheme 3: Conversion of 4 to 1. a) 20 mol % Co(acac)2, PhSiH3, 1 atm O2, THF, 0°C, 82%, diastereomeric ratio ...