By J R Hanson; R B Boar; Royal Society of Chemistry.; et al

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Sheldrick, Phytochemistry, 1980, 19,869. E. W. Warnhoff, P. Reynolds-Warnhoff, and M. Y. H. Wong, J. A m . Chem. , 1980,102,5956. J. E. McMurry and W. , 1980, 21, 2477. Sesquiterpenoids 39 of the two panasinsenes. X-Ray analysis has been used to determine the structure of the unique alcohol (256) named koraiol, which is isolated from Pinus k o r i c e n ~ i s . ~It' ~is suggested that this compound may be derived from humulene rather than caryophyllene since the gem-dimethylcyclobutane ring is cis-fused.

E. Cane and R. B. , 1980, 21,437. J. R. Hanson, T. Marten, and R. Nyfeler, J. Chem. ,Perkin Trans. I , 1976, 876. H H (288) Scheme 28 derived from the pro-5R hydrogen of mevalonate, but it is not absolutely clear whether this hydrogen originates from C-1 or C-9 of farnesyl pyrophosphate. '27These compounds cooccur with a number of other known vellerane sesquiterpenoids which have been isolated previously from Lacturius species. Two related compounds, blennin A (297) and blennin D (298), have been isolated from Lucturius blennius.

Painter,-111,J. Org. 45, 3989. B. B. Jarvis, J. 0. Midiwo, and E. P. , 1980, 21, 787. R. M. Eppley, E. P. Mazzola, M. E. Stack, and P. A. Dreifuss, J. Org. , 1980,45, 2522. W. Breitenstein, C. Tamm, E. V. Arnold, and J. Clardy, Helv. Chim. Acra, 1979, 62, 2699. 18 Terpenoids and Steroids The wide range of important biological properties of a number of trichothecane sesquiterpenoids has stimulated a considerable flurry of synthetic interest in this area. 62"In a new approach to the synthesis of H H - Reagents: i, PhCONMe,-COCl,; ii, H,S-py; iii, Bu,SnH; iv, NaOMe; v, ClSiMe,Bu'-Et,N; Ac,O-py; vii, Bu,NF; viii, MsCl vi, Scheme 11 trichodermol (13l ) , Still and T ~ a have i ~ ~constructed a bicyclic intermediate (132) with the correct relative stereochemistry by a Diels-Alder reaction followed by a subsequent P-oxido fragmentation (Scheme 12).

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