Studies toward the total synthesis of cyclodidemniserinol trisulfate. Part I: 3,5,7-Trisubstituted 6,8-dioxabicyclo [3.2.1] octane core structure construction via a convergent and a linear stereoselective synthesis
✍ Scribed by Jian-Hua Liu; Lai-Dong Song; Ya-Qiu Long
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 533 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The core structure of the natural product cyclodidemniserinol trisulfate, a natural HIV-1 integrase inhibitor, was synthesized by employing intramolecular ketal formation strategy via a convergent synthesis and a linear synthesis approach, respectively. Both approaches relied on Shapless asymmetric dihydroxylation to introduce the chiral centers at 1-and 7-position, and the latter also utilized Sharpless asymmetric epoxidation to install the chiral center at 3-postion of the 3,5,7-trisubstituted-6,8-dioxabicyclo [3.2.1] octane. The established methodologies will be beneficial for further total synthesis and structural derivatization.