The total synthesis of (±)-arisugacin A
✍ Scribed by Kevin P. Cole; Richard P. Hsung; Xiao-Fang Yang
- Book ID
- 104250970
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 142 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A 20-step total synthesis of (±)-arisugacin A with an overall yield of 2.1% is described here. This synthesis features highly convergent formal [3+3] cycloaddition and a strategic dihydroxylation-deoxygenation protocol leading to the desired angular C12a-OH.
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The first enantioselective synthesis of (-)-arisugacin A in 17 steps is described here, featuring a CBS asymmetric ketone reduction and a highly stereoselective formal [3+3] cycloaddition approach. This concise synthesis of the enantiomer unambiguously confirms the original assignment of the absolut