191861-69-5Relevant academic research and scientific papers
A cycloaddition approach to breynolide
Martin, Stephen F.,Anderson, Bruce G.,Daniel, Dilon,Gaucher, Anne
, p. 8997 - 9006 (2007/10/03)
A novel approach to the functionalized hydrobenzothiophene subunit of the sesquiterpene breynolide (3) has been developed. The sequence features the Diels-Alder reaction of the vinyl sulfones 12 and 13 with the Danishefsky diene 9 to give the cycloadducts 14 and 16 as the major products. Reduction of the sulfone moieties of 14 and 16 gave the sulfides 20 and 21, respectively. Subsequent dipolar cycloaddition of 20 and 21 with a functionalized nitrile oxide gave the corresponding adducts 24 and 25, which possess functionality suitable for elaboration into breynolide (3).
A novel approach to breynolide
Martin,Daniel
, p. 4281 - 4284 (2007/10/02)
The viability of the key steps in our approach to the novel sesquiterpene breynolide (1) has been verified by preparation of the hydrobenzothiophene 16. The sequence features a Diels-Alder reaction of 10 with 7 to lead eventually to 13; subsequent dipolar
