-)-Quinic acid in organic synthesis. 1. A facile synthesis of 2- crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone
β Scribed by Tony K.M. Shing; Ying Tang
- Book ID
- 108374282
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 695 KB
- Volume
- 46
- Category
- Article
- ISSN
- 0040-4020
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π SIMILAR VOLUMES
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.
A new and efficient route to (-)-(1R,2R,4R,6S)-l,6-epoxy-4-benzyloxycyclohexan-2-ol is described starting from (-)-quinic acid. The pivotal step involves a La3+-induced reversal of the diastet~eoselectivity for the borchydride reduction of an imm'medi~ cyclnhexan-4-one. (IR,2R,4R,6R)-6-Propyloxycycl