Total synthesis of twelve membered resorcyclic acid lactones, (R)-penicimenolide A, (R)-resorcyclide and (R)-dihydroresorcyclide
| Title | Total synthesis of twelve membered resorcyclic acid lactones, (R)-penicimenolide A, (R)-resorcyclide and (R)-dihydroresorcyclide |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Das, P, D. Reddy, S |
| Journal | Tetrahedron |
| Volume | 85 |
| Pagination | 132059 |
| Date Published | APR |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | Macrocycle, Natural product, organic synthesis, Total synthesis |
| Abstract | Resorcyclic Acid Lactones or RALs are a class of fungal secondary polyketides isolated from a variety of fungal strains like Lasiodiplodia theobromae, Penicillium sp., Syncephalastrum racemosum etc. This class of macrocyclic lactones are found to exhibit a broad spectrum of biological activities and are of significant synthetic importance. Herein, we report the first total synthesis of (R)-penicimenolide A, twelve membered RAL (RAL12) isolated from Penicillium sp. (NO. SYP-F-7919). Besides, we also report the total synthesis of two other members, namely, (R)-trans-resorcyclide and (R)-dihydroresorcyclide. In the course of synthesis, we have utilized ring closing metathesis (RCM) as the key step in constructing the core macrolactone scaffold. (C) 2021 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2021.132059 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.233 |