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Synthesis of scillascillin, a naturally occurring benzocyclobutene

✍ Scribed by Viresh H. Rawal; Michael P. Cava

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
185 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The novel homoisoflavanone scillascillin has been synthesized from phloroglucinol. The sequence described represents the first synthesis of a naturally occuring benzocyclobutene.

The first example of a silyl transfer involving an 8-membered transition state is reported.

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I'mted 8x1 Cm11 Bnta~n. B. SIMOSLW and P. BILASSA~D 781 yield OP the corresponding products in a 2.9: 1.0 ratio). A combination consisting largely oP the E-isomer could also be obtained by the use oP trimethylsilyl triilate in triethylamine" but the yield did not exceed 561. Analogoua compounds ha