Facile synthesis of the cyclopentane moiety of (all-E,2R,5R,6S)-2,6-cyclolycopene-1,5-diol
β Scribed by Bruno Traber; Hanspeter Pfander
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 72 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
2,6-Cyclolycopene-l,5-diol (3) was synthesized in 9 steps starting from Β’t-terpinyl acetate (11). This represents the first total synthesis of an oxidative metabolite of lycopene (2). The synthesis was performed according to a C~.s + C~o + Cm5 = C40 strategy using the Wittig olefination to couple th
Sch611kopf's auxiliary 16 was added to bis-lactim iodide 21 to give 1,2-bis[(3S,6R)-3,6dihydro-2,5-dimethoxy-3-isopropylpyrazin-6-yl]ethane 22 in 50% d,e. Dimer 22 was separated from its diastereoisomer 23 and deprotected using 6M HCI to afford homochiral (2R,5R)-2,5-diaminohexan-1,6dioic acid 24.