Total Syntheses of (−)‐Huperzine Q and (+)‐Lycopladines B and C

Abstract

Utilizing a late-stage enamine bromofunctionalization strategy, the twelve-step total synthesis of (-)-huperzine Q was accomplished. Furthermore, the first total syntheses of (+)-lycopladines B and C are described. An unprecedented X-ray crystal structure of an unusual epoxyamine intermediate is also reported, and the synthetic application of this intermediate in natural product synthesis is demonstrated.

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

“…Then, the resulting enolate was approached by an aldehyde from the opposite side to the newly attached vinyl group. A similar stereochemical outcome of such transformation has been already reported [26–33]. Moreover, the addition of aldehyde gave rise to the anti aldol product (both in 25 and 26 ).…”

“…A copper-catalyzed 1,4-addition of organometallic reagents to cyclic α,β-unsaturated ketones, followed by an aldol reaction has been already used in the synthesis of complex natural products [26–33]. Although this approach is challenging in terms of diastereoselectivity (up to eight possible diastereoisomers), it enables a rapid increase of molecular complexity.…”

Scaffold Diversity Synthesis and Its Application in Probe and Drug Discovery

“…[49] Thew ay that biosynthetic strategies employ divergent intramolecular cyclizationso facommon intermediate to produce diverse arrays of scaffolds inspired Mizoguchi et al to employ dehydrosecodine (73;S cheme 6) as ac ommon Scheme6. Biosynthesis-inspired approach to furnish diverse alkaloidal scaffolds.…”

Atom Efficient Magnesiation of N‐Substituted Alkyl Indoles with a Mixed Sodium‐Magnesium Base

“…N-methylindole was purchased from Aldrich and stored over 4 Å molecular sieves. N-ethylindole, [24] N-isopropylindole, [25] nBuNa, [26] and Mg(CH 2 SiMe 3 ) 2 [14] were prepared according to literature procedures.…”