Unified approach for the total synthesis of Bis-THF C-15 acetogenins: a chloroenyne from laurencia majuscula, laurendecumenyne B and laurefurenynes A/B
| Title | Unified approach for the total synthesis of Bis-THF C-15 acetogenins: a chloroenyne from laurencia majuscula, laurendecumenyne B and laurefurenynes A/B |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Senapati, S, Unmesh, NA, Shet, MN, Ahmad, I, Ajikumar, N, Ramana, CV |
| Journal | Synthesis-Stuttgart |
| Volume | 53 |
| Issue | 16 |
| Pagination | 2903-2910 |
| Date Published | AUG |
| Type of Article | Article |
| ISSN | 0039-7881 |
| Keywords | bis-THF C-15 acetogenins, carbohydrate building block, relay-cross-metathesis, S(N)2 halogenation, Sharpless asymmetric dihydroxylation-cycloetherification |
| Abstract | A highly diastereoselective total synthesis of several bis-THF C-15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenyries A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, S(N)2 halogenation, and a relay cross metathesis. |
| DOI | 10.1055/a-1500-1407 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.157 |
Divison category:
Organic Chemistry
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