Decahydronaphthoic Acids and their Relationship to the Decalols and Decalylamines.¹ A Stereochemical Study of the Reaction of Nitrous Acid with Decalylamines

Multicomponent NMR Titration for Simultaneous Measurement of Relative pKas

“…20 Each alcohol was converted to the corresponding ketone by chromic acid oxidation. 21 A mixture (72:28) of the cis stereoisomers (3 cc , 3 ct ) and a separate mixture (70:30) of the trans stereoisomers (3 tc , 3 tt ) of 2-decalylamine (decahydro-2-naphthaleneamine) were prepared by reductive amination of the corresponding cis or trans ketone with ammonium acetate and sodium cyanoborohydride. 22 Spectral Assignments.…”

Microbial Resolution of (±)-1 and 2-Decalols

“…And, lithium aluminum hydride reduction of V gave a mixture of 30 % of (±)-trans,trans-l-decalol (la, Ib) and 70 % of (±) -trans,cis-l-decalol (lIa, lIb). A similar mixture (la, Ib and lIa, lIb) has already been obtained by sodium borohydride reduction of V by Monson et af.3) Microbial hydrolysis of a mixture of (±)-trans, trans and trans,cis-l-decalyl 2) Micro- Dauben et al 5 ) reported that hydrogenation of a-naphthol using Adams' catalyst in acetic acid afforded (±)-cis,trans-l-decalol (IVa, IVb) mp 93°C (mp 88 ~ 89°C by Zimmerman et al 6 »). By the same method, we could obtain (±)-cis,trans-l-decalol (IVa, IVb), mp 91 ~ 91SC (cis-a-decalol 1)4) from the products which corresponded to the fourth peak in the gas chromatogram of Fig.…”

Cytochalasin support studies. Macrocycle synthesis via enolate-assisted, intraannular 1,4-fragmentation reactions

“…The ether was dried (MgS04) and evaporated in vacuo. Distillation of the crude residue (142 °C, 2 mmHg) afforded 6.5 g (86%) of a colorless oil: TLC (1,0.53); mass spectrum mje 250 (M+, caled for C,sH22 0 3 2 5 0.157, found 250.158, <l), 204 (30). 144 (100); IR (neat) 5.75 and 5.83 µ (C=0); 61.6 (CH2), 44.7 (C), 38.5, 36.5, 30.1, 28.9, 24.4, 22.9, 22.5, 14.0 ppm.…”