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| Type |
Oral Presentation |
| Area |
Oral Presentations for Young Scholars in Organic Division |
| Room No. |
Room 301+302 |
| Time |
THU 09:30-09:45 |
| Code |
ORGN.O-3 |
| Subject |
Memory of Chirality approach to the asymmetric total synthesis of Salinosporamide B |
| Authors |
Soojun Park, Sanghee Kim1,*
College of Pharmacy, Seoul National University, Korea
1College of Pharmacy / Department of Pharmacy, Seoul National University, Korea
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| Abstract |
The term, “Memory of Chirality (MOC)”, describes a phenomenon in which the chirality of the starting material is preserved in a reactive intermediate for a limited time. Although MOC is an attractive strategy for asymmetric synthesis, only a few applications of MOC to total synthesis have been reported. Using the principles of MOC, we performed a concise asymmetric total synthesis of Salinosporamide B. Our key step, one-pot intramolecular Aldol reaction and hydrolysis, proceeded with a high level of chirality preservation and complete diastereoselectivity without the aid of external chiral sources. To finalize the total synthesis, we also focused on one-pot oxidation and Barbier type addition after lactam ring formation step. This study represents a significant advance in the synthetic utility of MOC. |
| E-mail |
crazywinter9@snu.ac.kr |
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123rd General Meeting of the KCS