Solutions_Manual_for_Organic_Chemistry_6th_Ed 315

Solutions_Manual_for_Organic_Chemistry_6th_Ed 315 - 1 4-24...

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Unformatted text preview: 1 4-24 The cyclization of squalene via the epoxide is an excellent (and extraordinary) example o f how n Nature uses organic chemistry to its advantage . I one enzymatic step, Nature forms four rings and eight chira l centers ! Out of 2 56 possible stereoisomers, only one is formed ! • HO \ 1 4-25 = bonds formed � H H :\. � � ,,----" :0 - CH3 • • - .. • H �CH3 H (b) OCH3 . � H OCH3 + : �-'C H 1 (a) 1 4-26 � O� O- Na+ H2N � (c) 0 _ Na+ � s � O- (d ) (J I � � o Na+ H N� OH (e) N (f) C� O- K+ : N == N == N � _' a O N+ + 1 4-27 (a ) OH HI 80 � " '" Et M ""- / (b) CH30 - Ho 0 H (c) (d) ..,. ,,, Et , Me ' , ,A'" , A o e H o "' " " Me C H30H • ' Et " 1 Me Me '>---f/ Me X3oH H " Me H H+ • CH30H CH30 � ;� "'- OCH3 OH " Me H 308 ...
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