Stereoelectronic factors in bridgehead C–H bond insertion: studies toward the total synthesis of maoecrystal V
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چکیده
منابع مشابه
11-Step Total Synthesis of (−)-Maoecrystal V
An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to a...
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The first total synthesis of (-)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (-)-maoecrystal Z in only 12 steps from (-)-γ-cyclogeraniol.
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Two strategies toward the total synthesis of maoecrystal V (1) culminating in the construction of core structures 2 and 3 are described.
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ژورنال
عنوان ژورنال: Tetrahedron
سال: 2016
ISSN: 0040-4020
DOI: 10.1016/j.tet.2016.03.101