Desymmetrisation of meso-2,4-Dimethyl-8-oxabicyclo[3.2.1]-oct-6-ene-3-ol and its Application in Natural Product Syntheses
- Title
- Desymmetrisation of meso-2,4-Dimethyl-8-oxabicyclo[3.2.1]-oct-6-ene-3-ol and its Application in Natural Product Syntheses
- Creator
- Tadiparthi K.; Anand P.; Sakirolla R.; Gupta T.P.; Jadhav K.A.; Kishore Das S.; Singh Yadav J.
- Description
- 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 (19952020) 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. 2021 The Chemical Society of Japan & Wiley-VCH GmbH
- Source
- Chemical Record, Vol-22, No. 3
- Date
- 2022-01-01
- Publisher
- John Wiley and Sons Inc
- Subject
- Chiral pool; Dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-ol; Hydroboration; Lactone; Natural products; Total synthesis
- Coverage
- Tadiparthi K., Department of Chemistry, CHRIST (Deemed to be University), Hosur Road, Bangalore, 560029, India, Natural Product Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India; Anand P., Department of Chemistry, CHRIST (Deemed to be University), Hosur Road, Bangalore, 560029, India; Sakirolla R., Department of Chemistry, Central University of Karnataka, Gulbarga, Karnataka, 585367, India, Natural Product Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India; Gupta T.P., School of Science, Indrashil University, Kadi, Mehsana, Gujarat, 382740, India; Jadhav K.A., School of Science, Indrashil University, Kadi, Mehsana, Gujarat, 382740, India; Kishore Das S., School of Science, Indrashil University, Kadi, Mehsana, Gujarat, 382740, India; Singh Yadav J., Natural Product Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India, School of Science, Indrashil University, Kadi, Mehsana, Gujarat, 382740, India
- Rights
- Restricted Access
- Relation
- ISSN: 15278999; PubMed ID: 34894063; CODEN: CRHEA
- Format
- Online
- Language
- English
- Type
- Article
Collection
Citation
Tadiparthi K.; Anand P.; Sakirolla R.; Gupta T.P.; Jadhav K.A.; Kishore Das S.; Singh Yadav J., “Desymmetrisation of meso-2,4-Dimethyl-8-oxabicyclo[3.2.1]-oct-6-ene-3-ol and its Application in Natural Product Syntheses,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 26, 2025, https://archives.christuniversity.in/items/show/15183.