176017-93-9Relevant academic research and scientific papers
Synthesis of (1S,5S)-4,5-dihydro-1,5-epoxy-1H-2-benzoxocin-6(3H)-one from (S)-malic acid derivatives
Wuensch, Bernhard,Diekmann, Heike
, p. 69 - 76 (2007/10/03)
The homochiral 1,3-dioxanes 8a-e with a 2-bromophenyl substituent in position 2 and an electrophilic group in position 4 were stereo- and regioselectively prepared from the (S)-malic acid derivatives 6a, 6b, 11, and 14. Attempts to prepare the tricycles 5a-c by connecting the 2-phenyl substituent with the electrophilic groups in position 4 of 8a-e in a Parham cyclization across the 1,3-dioxane ring failed. The synthesis of the tricyclic title ketone 5a succeeded, however, by addition of the lithiated benzaldehyde acetal 7c to the protected α-hydroxylactone 10b and subsequent treatment of the intermediate ketone 23 with acid. The acid hydrolysis of the alcohol 26, which was obtained by addition of 7c to the protected dihydroxy aldehyde 25b, followed by oxidation of the resulting alcohols 27 a and b represent a second possibility for the preparation of the tricyclic ketone 5a. VCH Verlagsgesellschaft mbH, 1996.
CNS AGENTS: OPTICAL RESOLUTION WITH BAKER'S YEAST AS KEY STEP IN THE SYNTHESIS OF OPTICALLY ACTIVE TRICYCLIC AMINES
Wuensch, Bernhard,Diekmann, Heike
, p. 709 - 712 (2007/10/02)
The synthesis of the optically active 1,5-epoxy-3,4,5,6-tetrahydro-N-methyl-1H-2-benzoxocin-6-amines ((-)-10) and ((+)-10) is achieved by optical resolution of the racemic 1,5-epoxy-4,5-dihydro-1H-2-benzoxocin-6(3H)-one ((+/-)-8) with baker's yeast as the key step. (+)-10 can also be prepared starting with the homochiral α-hydroxy-γ-butyrolactone ((-)-6a), which is easily obtained from (S)-(-)-malic acid.
