130626-32-3Relevant 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.
A FORMAL SYNTHESIS OF APLASMOMYCIN. ASSEMBLY OF THE C3-C17 SEGMENT BASED ON 1,3- AND 1,5- ASYMMETRIC REDUCTIONS
Matsuda, Fuyuhiko,Tomiyoshi, Nobuya,Yanagiya, Mitsutoshi,Matsumoto, Takeshi
, p. 3469 - 3488 (2007/10/02)
The C3 - C17 segment of a boron containing ionophoric antibiotic aplasmomycin (1), the key intermediate in Corey's total synthesis of 1, was stereoselectively synthesized in an optically active form.This synthesis involved stereoselective construction of the two segments, (+)-dithiane 3 (C3-C11) and (+)-aldehyde 4 (C12-C17), based on remote controlled asymmetric reductions of the corresponding ketones as key steps and connection of 3 and 4 through the trans-double bond to elaborate the (+)-dithiane 2 (C3-C17), the key intermediate in Corey's total synthesis of 1.
A Formal Synthesis of Aplasmomycin. Assembly of the C3-C17 Segment Based on Remote Controlled Asymmetric Reductions
Matsuda, Fuyuhiko,Tomiyosi, Nobuya,Yanagiya, Mitsutoshi,Matsumoto, Takeshi
, p. 2097 - 2100 (2007/10/02)
The C3-C17 segment of a boron containig ionophoric antibiotic aplasmomycin (1), the key intermediate in Corey's total synthesis of 1, was stereoselectively synthesized in an optically active form through remote controlled asymmetric reductions.
