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Stereoselective synthesis of an isomer of Membrenone-C via an aldol based two directional chain extension

✍ Scribed by Michael V. Perkins; Rebecca A. Sampson

Book ID: 104260088
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 271 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01846-2

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✦ Synopsis

An isomer of Membrenone-C was prepared in 8 steps (17% yielu) with 93% overall ds starting from the ethyl ketone (S)-10. Key steps are the boron-mediated aldol followed by anti selective reduction, giving the C6-C10 stereochemistry, the two direction chain extending double titanium aldol coupling, 16 + 20 -o 19, and the TFA promoted double cyclisation/dehydration giving an isomer of Membrenone-C, 21 -o 4.

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