By John ApSimon
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Additional resources for The total synthesis of natural products Volume 2
In a d d i t i o n , h e a t i n g t h e mixture of c i t r a l a and c i t r a l b t o over 130' causes i s o m e r i z a t i o n t o a t h i r d isomer, i s o c i t r a l (E),t o occurq9 ( i n a d d i t i o n t o c y c l i z a t i o n r e a c t i o n s t h a t occur a t h i g h e r temperatures and under t h e z). *The c o n d i t i o n s necessary f o r high conversion t o t h e h y d r a t e have been examined by s e v e r a l a u t h o r s ( s e e , e . g . , Ref. 9 8 ) . 28 The S y n t h e s i s of Monoterpenes i n f l u e n c e of a c i d c a t a l y s t s * ) .
A l s o s t a r t s from R - l i n a l y l a c e t a t e r e a c t i o n of N-bromosuccinimide on which gives a mixand from which hydroture of t h r e e bromacetates gen bromide can be remved by d i e t h y l a n i l i n e , leading t o t h e a c e t a t e (57) o f t h e R-isomer, from which t h e alcohol (55) can be obtained by conventional h y d r o l y s i s . 09 (s), =,=, =, Og/h~/sens ____c 6a I (5 R- OCOCH 3 R- f O C H 3 R- + + q0c0cH3 OCOCH 3 Br CH2Br 56a BrCH2 56b - 56c - 26 The S y n t h e s i s of Monoterpenes 2-Methyl-6-methyleneocta-2,7-diene-4-01 methylene-oct-7-en-4-01 (63) (62) and 2-Methyl-6- These two aocohols were i s o l a t e d from t h e s e x a t t r a c t a n t of t h e bark b e e t l e , Ips c o n f u s ~ s ,and ~ ~ have been s y n t h e s i z e d by Reece e t a l .
Scheme 10 OH Y OH HO s+. / I'OH 107b - 107a - CbHgLi 8% 38 9% 14% Substances Derived from Chrysanthemic Acid 39 Sucrow and Richter's synthesis of the Chrgtien-Bessisre monoterpene (Z)lz7 is illustrated in Scheme 11,13' and Sucrow's Scheme 11 H3C\ /CH3 C -CH -CH =C\ H3C/ IOH CH2 I CH3 I 1. H202 ___c 2. 140 The principal of the two syntheses is practically the same as for the same author's earlier santolinatriene synthesis (see above). -CH=CHOCH3 H5C202C'IOH 1. LiAlH4 2. H ~ O + c *In Scheme 12, the alcohol (E) is acetylated (to before proceeding with the lithium t-butoxyaluminm hydride reduction.