Synthetic studies on (±)-antheridic acid; construction of the antheridic acid skeleton
✍ Scribed by Masanao Shimano; Hiroto Nagaoka; Yasuji Yamada
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 231 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
An effective route for the total synthesis of antheridic acid (1) has been devised in which the initial chiral intermediate 7 is generated by enantioselective catalytic reduction and transformed in a stereocontrolled fashion into key intermediates 9, 10, 13, and 2.
Hydroxypicrasan-3-one, a compound having the correct relative stereochemistry of al1 the six ring-juncture chira1 centers of the picrasane skeleton, was synthesized from a known tricyclic compound, using the orthoester Claisen rearrangement and lead tetraacetate oxidation as key reactions.
A highly functionalized cyclopentene carboxylic acid derivative, as an advanced synthetic intermediate of viridenomycin, was synthesized. The synthesis commenced with the previously reported highly functionalized tetrahydrofuran derivative prepared from D-glucose. The stereochemical confirmation of