66333-29-7Relevant articles and documents
A Unified Approach for the Assembly of Atisine- and Hetidine-type Diterpenoid Alkaloids: Total Syntheses of Azitine and the Proposed Structure of Navirine C
Liu, Jie,Ma, Dawei
supporting information, p. 6676 - 6680 (2018/05/03)
A tetracyclic dinitrile was synthesized in twelve steps from cyclohex-2-en-1-one by using a chelation-triggered conjugate addition to a γ-hydroxy-substituted α,β-unsaturated nitrile and an oxidative dearomatization/Diels–Alder cycloaddition cascade as the key steps. The first total synthesis of azitine (in 17 steps) was achieved through a simple reductive cyclization of this intermediate and subsequent transformations while the total synthesis of the proposed structure of navirine C (in 19 steps) was accomplished by a hydrogen-atom-transfer reaction of the tetracyclic dinitrile, Pd/C-catalyzed reductive cyclization, and subsequent functional group manipulation.
Skeletal and stereochemical diversification of tricyclic frameworks inspired by Ca2+-ATPaSe inhibitors, artemisinin and transtaganolide D
Oguri, Hiroki,Yamagishi, Yutaka,Hiruma, Takahisa,Oikawa, Hideaki
supporting information; experimental part, p. 601 - 604 (2009/09/25)
(Chemical Equation Presented) Inspired by the common skeletal motifs of Ca2+-ATPases inhibitors involving artemisinin and transtaganolide D, small molecule collections with the three-dimensional structural diversity of tricyclic systems were designed and expeditiously synthesized (4-5 steps). A synthetic strategy featuring stereochemical diversification of ring-junctions and control of cyclizatlon modes was devised to access varied molecular architectures in a systematic fashion.
ALLYLIC REARRANGEMENT OF CYANOPHOSPHATE. II. SYNTHESIS OF β-CYANO-α,β-UNSATURATED KETONES
Kurihara, Takushi,Miki, Masuo,Yoneda, Ryuji,Harusawa, Shinya
, p. 2747 - 2753 (2007/10/02)
Boron trifluoride-catalyzed allylic rearrangement of the cyanophosphates of α,β-unsaturated ketones (1a-d, 7 and 14) was found to give the allylic phosphates (3a-d, 9 and 16), which were successfully converted to β-cyano-α,β-unsaturated ketones (6a-d, 13 and 20) by acid hydrolysis (0.5 N HCl) followed by manganese dioxide oxidation of the resulting allylic alcohols(5a-d, 11, 12 and 17).The stereochemical features of the allylic phosphates (9 and 16) are discussed.Keywords-α,β-unsaturated ketone; diethyl phosphorocyanidate; cyanophosphate; allylic rearrangement; boron trifluoride etherate; manganese dioxide; β-cyano-α,β-unsaturated ketone
