| Title: | "Study of the beta-oxygen effect in the Barton-McCombie reaction for the total synthesis of (4R,5R)-4-hydroxy-gamma-decalactone (Japanese orange fly lactone): a carbohydrate based approach" |
| Author(s): | Desireddi JR; Rao MM; Murahari KK; Nimmareddy RR; Mothe T; Lingala AK; Maiti B; Manchal R; |
| Address: | "Aragen life sciences Private Limited (formerly known as GVK Biosciences Private Limited), Medicinal Chemistry Division 28A, IDA Nacharam Hyderabad-500076 Telangana India janardanareddi@gmail.com. Department of Chemistry Chaitanya (Deemed to be University) Warangal-506001 Telangana India ravinder@chaitanya.edu.in. Accrete Pharmaceuticals Private Limited Tangadpalli Village, Choutuppal Mandal, Yadadri Bhuvanagiri District-508252 Telangana India" |
| ISSN/ISBN: | 2046-2069 (Electronic) 2046-2069 (Linking) |
| Abstract: | "Efficient and facile synthesis of Japanese orange fly lactone (1) was achieved from a commercially available d-glucose by investigating the Barton-McCombie reaction with furanose anomeric isomers (12alpha , beta) with an overall yield of 12.6%. During the course of this synthesis, the beta-oxygen effect was discovered in the deoxygenation step at the C-3 position using the Barton-McCombie reaction, where the substrate allows the effect to operate in one of the isomers but not in the other. Under the same reaction conditions, xanthate derived from the beta-furanose isomer affords a high yield of deoxygenated product, whereas the alpha-isomer produces a very low yield. The key transformations used were Wittig olefination, TEMPO mediated oxidation, and Barton-McCombie deoxygenation, resulting in a concise total synthesis of Japanese orange fly lactone (1). Our success will allow for further biological studies of this natural product, as well as opportunities for developing new potentially promising pheromones" |
| Notes: | "PubMed-not-MEDLINEDesireddi, Janardana Reddi Rao, Mora Mallikarjuna Murahari, Kiran Kumar Nimmareddy, Rajashekar Reddy Mothe, Thirupathi Lingala, Arun Kumar Maiti, Bhimcharan Manchal, Ravinder eng England 2022/10/07 RSC Adv. 2022 Sep 7; 12(39):25520-25527. doi: 10.1039/d2ra04531a. eCollection 2022 Sep 5" |
