Convenient Synthesis of (3R, 4S)-4-Methyl-3-hexanol and (S)-4-Methyl-3-hexanone, the Pheromones of Ants

Dhotare, Bhaskar; Hassarajani, S. A.; Chattopadhyay, Angshuman

doi:10.3390/50801051

Cited by 3 publications

(2 citation statements)

References 9 publications

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“…The conversion of the 1,2‐diol into a double bond was first attempted through a dimesylate. Thus, the treatment of 6 with MsCl/Et 3 N/DMAP15 led to 7 , which upon exposure to Zn/I 2 in refluxing DMF resulted in alkene 8 in 70 % yield (from 6 ). The same conversion could be more conveniently realized under Ph 3 P/imidazole/I 2 /THF conditions16 to give 8 in essentially 100 % yield.…”

Section: Resultsmentioning

confidence: 99%

A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols

et al. 2014

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RNA repair is an emerging strategy for gene therapy. Conventional gene therapy typically relies on the addition of the corrected DNA sequence of a defective gene to restore gene function. As an additional option, RNA repair allows alteration of the sequence of endogenous messenger RNAs (mRNAs). mRNA sequence alteration is either facilitated by intracellular spliceosome machinery or by the intrinsic catalytic activity of trans‐acting ribozymes. Previously we developed twin ribozymes, derived from the hairpin ribozyme, by tandem duplication and demonstrated their potential for patchwise RNA repair. Herein we describe the development of such a twin ribozyme for potential repair of a deletion mutation in the oncogenic CTNNB1‐ΔS45 mRNA. We demonstrate that hairpin ribozyme units within the twin ribozyme can be adapted to efficiently cleave/ligate non‐consensus substrates by introduction of compensatory mutations in the ribozyme. Thus, we show the twin ribozyme mediated repair of truncated CTNNB1 transcripts (up to 1000 nt length). Repair of the entire CTNNB1‐ΔS45 mRNA, although apparently possible in general, is hampered in vitro by the secondary structure of the transcript.

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Section: Resultsmentioning

confidence: 99%

A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols

et al. 2014

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“…In the synthesis of (2S,3S,7S)-56, a methyl branch at the 7-position in a C 15 chain was constructed by alkylation of a chiral 2-ethyloxazoline (R-1-1), 174 which was prepared by condensing For the synthesis of (3R,4S)-42, (R)-2,3-cyclohexylideneglyceraldehyde, which was prepared from D-mannitol, was utilized (R-1-2a). 129 Crotylation of the aldehyde predominantly produced a threo-alcohol that included a tertiary carbon with an S conguration, which was benzylated and, subsequently, deketalized to produce 3-benzyloxy-4methyl-5-hexene-1,2-diol, a key intermediate of the pheromone. (S)-70 with a methyl branch at the 3-position in a C 8 chain was synthesized from glyceraldehyde acetonide, which was also prepared from D-mannitol (R-1-2b).…”

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

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Insect pheromones are some of the most interesting natural products because they are utilized for interspecific communication between various insects, such as beetles, moths, ants, and cockroaches. A large number of compounds of many kinds have been identified as pheromone components, reflecting the diversity of insect species. While this review deals only with chiral methyl-branched pheromones, the chemical structures of more than one hundred non-terpene compounds have been determined by applying excellent analytical techniques. Furthermore, their stereoselective syntheses have been achieved by employing trustworthy chiral sources and ingenious enantioselective reactions. The information has been reviewed here not only to make them available for new research but also to understand the characteristic chemical structures of the chiral pheromones. Since biosynthetic studies are still limited, it might be meaningful to examine whether the structures, particularly the positions and configurations of the branched methyl groups, are correlated with the taxonomy of the pheromone producers and also with the function of the pheromones in communication systems.

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