Desymmetrisation of meso‐2,4‐Dimethyl‐8‐oxabicyclo[3.2.1]‐oct‐6‐ene‐3‐ol and its Application in Natural Product Syntheses

• Published in: Chemical record Vol. 22; no. 3; pp. e202100286 - n/a
• Main Authors: Tadiparthi, Krishnaji, Anand, Pragya, Sakirolla, Raghavendra, Gupta, T. Prakash, Jadhav, Krishna A, Kishore Das, Sukant, Singh Yadav, Jhillu
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01.03.2022
• Subjects: Asymmetric synthesis; Biological activity; Biological Products; Chiral pool; Dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-ol; Functional groups; Hydroboration; Lactone; Natural products; Stereoisomerism; Synthesis; Total synthesis; Lactone; Dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-ol; Hydroboration; Chiral pool; Natural products; Total synthesis
• ISSN: 1527-8999; 1528-0691
• DOI: 10.1002/tcr.202100286

The compounds containing chiral centers and different functional groups serve as magnificent building blocks for the preparation of various natural products that are having immense biological activity. “Dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol” is one of the wonderful synthons to construct multiple stereo centers at a time during the asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various simple and complex natural products from the past three decades (1995–2020) by using dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol as a synthon. Moreover, the synthetic utility of this starting material was investigated and well demonstrated. Further, we executed the desymmetrization of dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol by hydroboration to get different chiral centers. After obtaining the stereocenters, we could manage either the fragment, formal or total synthesis of natural products, by simple protection and deprotection sequence followed by C−C bond formation steps. “Dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol” is one of the wonderful synthons to construct multiple stereo centers at a time during the asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various simple and complex natural products from the past three decades (1995–2020) by using dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol as a synthon. Moreover, the synthetic utility of this starting material was investigated and well demonstrated. Further, we executed the desymmetrization of dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol by hydroboration to get different chiral centers. After obtaining the stereocenters, we could manage either the fragment, formal or total synthesis of natural products, by simple protection and deprotection sequence followed by C−C bond formation steps.