Hideo Tanino

On the structure of the Diels-Alder adducts obtained from (E)-3-methoxycarbonylmethylene-2-oxoindoline with unsymmetrical butadiene derivatives

The Diels-Alder reaction of (E)-3-methoxycarbonylmethylene-2-oxoindoline with trans- and cis-1,3-pentadienes gave a single product, respectively, in high yield. The structural features of these adducts were elucidated by proton nmr analysis and chemical transformations

Total synthesis of (±)-surugatoxin☆

Abstract Total synthesis of surugatoxin 1 , isolated from the toxic Japanese ivory shell ( Babylonia japonica ), was achieved from 6-bromoisatin by a stepwise ring construction involving two key steps: the stereospecific cyclization ( 17 → 18 ) and hydration ( 33b → 1 ).

Total synthesis of neosurugatoxin

Abstract Total synthesis of neosurugatoxin 2 , having a strong affinity for nicotinic receptors, in described.

Total synthesis of (-+)-surugatoxin

Abstract Total synthesis of surugatoxin 1, isolated from the toxic Japanese ivory shell ( Babylonia japonica ), was achieved from 6-bromoisatin by stepwise ring construction involving two key steps: the stereospecific cyclization (9→10) and hydration (17→1).

Synthesis of (±)-prosurugatoxin and ring transformation of prosurugatoxin into surugatoxin

Abstract Synthetic identification of prosurugatoxin and data indicating a possible mechanism for the ring transformation of prosurugatoxin into surugatoxin are presented.

Asymmetric synthesis of the pentacyclic ring system of Aspidosperma alkaloids

Abstract The asymmetric synthesis of pentacyclic compound 13, a known intermediate in the synthesis of l-acetylaspidospermidine, was conducted via the condensation of 2-hydroxytryptamine with chiral C9 lactone 9, readily available from triol 4.

Synthesis of (±)-Prosurugatoxin and Ring Transformation of Prosurugatoxin into Surugatoxin

Synthetic identification of prosurugatoxin and a possible mechanism for the ring transformation of prosurugatoxin into surugatoxin are presented

Model experiments on surugatoxin synthesis. an approach in the construction of the pentacyclic ring system

Synthesis of the ethyl ester 2a of the debromo-aglycone of surugatoxin 1 has been achieved in 10 steps starting from readily available ethyl 2-(2-oxo-3-indolenyl)-3-oxo-4-phthalimidobutyrate 3.

Total synthesis of (−)-vallesamidine

Abstract A new synthetic method of (−)-vallesamidine, including a unique 2,2,3-trialkylindoline skeleton, is developed by reductive radical cyclization reaction from the 2,3-dialkylindole derivative, which has been known to be an intermediate for the synthesis of aspidospermidine.

A New Hexagonal Cyclic Enol Phosphate of 6-b-Hydroxypropionyllumazines from the Marine Swimming Polychaete, Odontosyllis undecimdonta

A new hexagonal cyclic enol phosphate of 6-β-hydroxypropionyllumazine and its 3-methyl and 1,3-dimethyl derivatives were isolated from Odontosyllis undecimdonta