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Stereoselective Synthesis of (+)-Goniothalesdiol
✍ Scribed by Prasad, Kavirayani R.; Gholap, Shivajirao L.
- Book ID
- 127287901
- Publisher
- American Chemical Society
- Year
- 2006
- Tongue
- English
- Weight
- 77 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
The first total synthesis of Goniothalesdiol A, isolated from the stems of Goniothalamus amuyon (Annonaceae) is reported. The C2 stereocentre and C3/C4 syn diol were created by a Sharpless kinetic resolution followed by acetonide formation. The tetrahydropyran ring was formed and the C6 stereocentre
## Abstract The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using D‐ribose as chiral precursor. The key steps involved are aryl __Grignard__ reaction, stereoselective alkoxy‐directed keto reduction, and intramolecular oxy‐__Micha
## Abstract Good to excellent stereoselectivities were achieved in the reductive cyclization (with Et~3~SiH/trimethylsilyl trifluoromethanesulfonate (TMSOTf)) of enantiopure hydroxy sulfinyl ketones en route to 2,5‐__cis__‐disubstituted tetrahydrofuran skeletons. Electrostatic effects of the exocyc