Total synthesis of protomycinolide iv
โ Scribed by Masanori Honda; Tsutomu Katsuki; Masaru Yamaguchi
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 288 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
A stereospecific sequence from the octalindlone 2 leads In 21 steps to the new lnsecttcrde ajuqarin-IV. Formation of the butenohde portion is conveniently achteved from acid 21 by successive use of the reaqents trts(tr~methylsiloxy)ethylene and ketenyhdenetrtphenyl-phosphorane.
The alkylation of (4,6-heptadien-3-one)-and (methyl 3,5-1aexadienoate)Fe(CO)3 (l and 2) were examined (0-42% de and 69-92% de respectively). Optically active (methyl 3,5-hexadienoate)Fe(CO) 3 (-)-2 was prepared by resolution of the corresponding carboxylic acid complex with 0t-methylbenzylamine.
Two chiral intenediates, C(l)-C( 9) and C(llI-Cc171 portions of protomycinolide IV, were synthesized both from (Sl-ethyl lactate via asymmetric pinacoZ-type rearrangement folZowed b2 diastereoselective reactions on cc-methyl-B,y-unsaturated carbonyl compounds.