The C 1 -C 11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C 6 and C 7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C 2 , C 3 hydroxyl groups, selective protection of t
Towards the total synthesis of clerocidin. Efficient assembly of the decalin subunit
✍ Scribed by István E Markó; Marianne Wiaux; Stuart M Warriner; Paul R Giles; Paul Eustace; David Dean; Marc Bailey
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 228 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Decalin 14, the fully-functionalised southern subunit of Clerocidin 1, a unique fungal metabolite, can be readily and stereoselectively assembled from diketone 7.
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The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular