𝔖 Bobbio Scriptorium
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Total synthesis of the muscarines

✍ Scribed by Michael C. Pirrung; Carl V. DeAmicis

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
277 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The total syntheses of racennc muscarme and allo-muscanne have been achieved usmg as a key step the stereospecific photochenucal rmg expansion of a cyclobutanone Muscanne (1) and affo-muscanne (2). components of the red fly aganc mushroom Amamta muscarza, were the

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The title total synthesis was achieved by a method featuring highly stereoselective intermolecular Diels-Alder reaction of the tetrahydroisobenzofuran 5 with the chiral butenolide 6 as the key step. The cycloadduct 4 was converted to the title alkaloid by way of the known sulfone 2 in 17 steps.