A stereoselective synthesis of the C15–C25 subunit of (+)-lasonolide A
✍ Scribed by Sung Ho Kang; Hyeong-wook Choi; Cheol Min Kim; Hyuk-Sang Jun; Suk Youn Kang; Joon Won Jeong; Joo-Hack Youn
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 157 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The C 15 -C 25 upper THP segment 2 of (+)-lasonolide A has been synthesized efficiently via diastereomeric differentiation, iodocyclization and Julia-Kocien ´ski's sulfone olefination to install its quaternary chiral center, cis-2,6-disubstituted THP and trans-olefin, respectively.
📜 SIMILAR VOLUMES
The stereocontrolled synthesis of a C15 C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and b-keto ester 7. The C25 C30 portion of dolabelides was prepared as well by ring
The C1-C16-segment of lasonolide A has been prepared stereoselectively in high chemical and optical yield starting from 2α-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (rac-1).
The C(18)-C(24) segment of lasonolide A has been prepared with complete chemodifferentiation of functionality.