397871-02-2Relevant academic research and scientific papers
Syntheses and Phytotoxicity of All Stereoisomers of 6-(2-Hydroxy-6-phenylhex-1-yl)-5,6-dihydro-2 H-pyran-2-one and Determination of the Effect of the α,β-Unsaturated Carbonyl Structure and Hydroxy Group Bonding to Chiral Carbon
Ochi, Ryota,Nishiwaki, Hisashi,Yamauchi, Satoshi
, p. 12558 - 12564 (2019/11/13)
All four stereoisomers of naturally occurring 6-(2-hydroxy-6-phenylhex-1-yl)-5,6-dihydro-2H-pyran-2-one (1) were synthesized by employing yeast-reduction products with high optical purity [from 95% enantiomeric excess (ee) to more than 99% ee], and then their phytotoxicities against lettuce and Italian ryegrass were evaluated. In the Italian ryegrass seedlings test, (6S,2′R)-1 showed the most potent and stereospecific activity against the shoots (IC50 = 260 μM) and roots (IC50 = 43.2 μM), with a significant difference from other stereoisomers. The highest seed germination inhibitory activity against Italian ryegrass seed was also observed in (6S,2′R)-1, showing a 53% germination ratio from the control at 1000 μM. This advantageous (6S,2′R) stereochemistry was employed in the syntheses of α,β-dihydro, 2′-dehydroxy, and 2′-methoxy derivatives 13-15. By the test using these derivatives, the importance of the α,β-unsaturated double bond and hydroxy group bonding to a chiral center on the 6-alkyl chain of 5,6-dihydro-α-pyrone for phytotoxicity was determined. In the test against lettuce, the 6S configuration and (6S,2′S) configuration were necessary for growth inhibition (IC50 = ca. 60 μM) and germination inhibition (63% germination ratio at 1000 μM), respectively.
A stereoselective aldol approach for the total syntheses of two 6-Alkylated 2H-pyran-2-ones
Rajaram, Singanaboina,Ramesh, Dasari,Ramulu, Udugu,Prabhakar, Peddikotla,Venkateswarlu, Yenamandra
, p. 112 - 121 (2014/02/14)
A simple and highly efficient stereoselective total synthesis of the 6-alkylated pyranones (6R)-6-[(1E,4R,6R)-4,6-dihydroxy-10-phenyldec-1-en-1-yl]- 5,6-dihydro-2H-pyran-2-one (1) and (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6- phenylhexyl]-2H-pyran-2-one (2) w
An organocatalytic route to the synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one and ravensara lactones
Dwivedi, Namrata,Tripathi, Divya,Kumar, Pradeep
, p. 1749 - 1756 (2012/02/03)
An organocatalytic enantioselective synthesis of the title compounds has been achieved. The stereogenic centers were generated by the iterative use of proline catalyzed α-aminoxylations and HWE olefination of aldehydes while the lactone ring was construct
An expedient stereoselective synthesis of the antifungal agent (6 S)-6-[(2 R)-2-hydroxy-6-phenylhexyl]-5,6-dihydro-2H-pyran-2-one
Narsaiah, A. Venkat,Ghogare, Ramesh S.
, p. 3271 - 3276 (2011/11/30)
An efficient and straightforward stereoselective synthesis of (6S)-6-[(2R)-2-hydroxy-6-phenylhexyl]-5,6-dihydro-2H-pyran-2-one is described. The chiral centers were generated by Sharpless asymmetric epoxidation followed by regioselective epoxide ring open
The stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy- 6-phenylhexyl]-2H-pyran-2-one via Prins cyclization
Yadav, Jhillu Singh,Chandrakanth, Dandekar,Rao, Yerragorla Gopala,Ravindar, Kontham,Subba Reddy, Basi V.
experimental part, p. 1432 - 1438 (2010/09/12)
The stereoselective total synthesis of an antiproliferative and antifungal a-pyrone natural product (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H- pyran-2-one is described. The key steps involved are the Prins cyclization, Mitsunobu reaction, and r
Stereoselective synthesis of (6S) and (6R)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one and their cytotoxic activity against cancer cell lines
Narasimhulu, Manchala,Krishna, Arepalli Sai,Rao, Janapala Venkateswara,Venkateswarlu, Yenamandra
experimental part, p. 2989 - 2994 (2009/06/20)
Stereoselective total synthesis of α,β-unsaturated lactone (1a), isolated from Ravensara crassifolia, has been achieved efficiently starting from chiral 2,3-O-isopropylidene-d-glyceraldehyde (3) followed by asymmetric allylation and ring-closing metathesi
Stereoselective total synthesis of a potent natural antifungal compound (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one
Das, Biswanath,Laxminarayana, Keetha,Krishnaiah, Martha,Kumar, Duddukuri Nandan
scheme or table, p. 6396 - 6398 (2010/05/02)
A practical stereoselective synthesis of (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one (1), a potent natural antifungal compound, is described. The sequence involves diastereoselective iodine-induced electrophilic cyclization, epoxide
Enantioselective total synthesis of the antifungal agent (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one
Sabitha, Gowravaram,Srinivas, Chitti,Sudhakar, Kadari,Rajkumar, Manne,Maruthi, Chittapragada,Yadav, Jhillu S.
, p. 3886 - 3890 (2008/09/17)
An enantioselective route for the synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one is reported. The synthesis is based on epoxide ring opening with a Grignard reagent and stereoselective reduction employing catecholborane as
Stereoselective synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one
Radha Krishna, Palakodety,Srinivas, Ravula
, p. 2197 - 2200 (2008/02/11)
A stereoselective synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one is reported. The strategy utilizes an olefin cross-metathesis, syn-benzylidene acetal formation and a preferential (Z)-Wittig olefination reaction and lactoniz
The first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one
Chandrasekhar,Narsihmulu, Ch.,Sultana, S. Shameem,Srinivasa Reddy
, p. 9299 - 9301 (2007/10/03)
Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifu
